CN102093216A - Method for preparing p-acetoxyacetophenone and o-acetoxyacetophenone - Google Patents
Method for preparing p-acetoxyacetophenone and o-acetoxyacetophenone Download PDFInfo
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- CN102093216A CN102093216A CN2009102274293A CN200910227429A CN102093216A CN 102093216 A CN102093216 A CN 102093216A CN 2009102274293 A CN2009102274293 A CN 2009102274293A CN 200910227429 A CN200910227429 A CN 200910227429A CN 102093216 A CN102093216 A CN 102093216A
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Abstract
The invention discloses a method for preparing p-acetoxyacetophenone and o-acetoxyacetophenone. The method comprises the following steps of: reacting p-hydroxyacetophenone and acetic anhydride for 1 to 3 hours at the temperature of between 40 and 50 DEG C by adding a catalytic amount of pyridine, and performing re-crystallization in cyclohexane after the reaction is completed to obtain a p-acetoxyacetophenone product; and reacting hydroxyacetophenone and acetic anhydride for 1 to 3 hours at the temperature of between 40 and 50 DEG C by adding a catalytic amount of concentrated sulfuric acid, washing the reaction solution after the reaction is completed, and performing re-crystallization by using 95 percent ethanol to obtain an o-acetoxyacetophenone product. The method has the advantages that: the raw material is low in price, experiment condition is mild, a few byproducts are generated in the experiments and yield is high, and the method has good popularization and application values.
Description
Technical field
The present invention relates to a kind of preparation method to acetoxy acetophenone and adjacent acetoxy acetophenone.
Background technology
To acetoxy acetophenone and adjacent acetoxy acetophenone is important medicine and fine-chemical intermediate, as acetoxy acetophenone being can be used for the preparation of information storage material photoresist material to acetoxy-styrene.The present domestic producer's large-scale production that do not have.
Below be existing several method for preparing parahydroxyacet-ophenone and o-hydroxyacetophenone:
(1) traditional method
The traditional preparation method of parahydroxyacet-ophenone and o-hydroxyacetophenone adopts two-step approach, promptly at first forms acetoxyphenyl by the phenol esterification, then at AlCl
3The Fries rearrangement reaction takes place down and gets in catalysis.Can outstandingly be mixed and heated to backflow as Lu of department of chemistry of Zhengzhou University and tell acetate, and then distill out acetoxyphenyl, yield 98% with phenol and diacetyl oxide; Chlorobenzene is that solvent, aluminum trichloride (anhydrous) are Lewis acid, drip acetoxyphenyl below 60 ℃, 60～65 ℃ were reacted 2 hours, treated parahydroxyacet-ophenone and the o-hydroxyacetophenone of getting, yield is respectively 69% and 23% (referring to " chemical reagent " 1993,15 (4): 254).This method esterification needs heating, and rearrangement product ortho position product yield is lower.
Kingdom's happiness of Anyang university chemistry engineering department is with the esterification of sulphuric acid catalysis phenol and diacetyl oxide, yield 96%; With composite catalyst NaCl-AlCl
3In the Fries of 240～250 ℃ of catalysis acetoxyphenyls rearrangement reaction, in 10 minutes reaction times, treated parahydroxyacet-ophenone and o-hydroxyacetophenone, yield are respectively 29% and 42% (referring to " Zhengzhou University's journal " 2000,32 (2): 89～90).This method esterification mild condition, the catalytic reaction times of composite catalyst is short, though rearrangement product ortho position yield increases, total recovery is lower.
(2) single stage method preparation
Phenol and Acetyl Chloride 98Min. are at AlCl
3Obtain 31.5% parahydroxyacet-ophenone and 68.5% o-hydroxyacetophenone under the catalysis through single step reaction, overall yield is 89% (referring to DE 3108076), and solvent that this method is used is chlorobenzene, and temperature of reaction is low, and the ortho position productive rate is lower, and total recovery has much room for improvement.
The Huang Liangbao of Nanjing University, Hu Wei etc. are raw material with phenol and diacetyl oxide, with 3～4 moles AlCl
3For the catalyzer single stage method makes parahydroxyacet-ophenone and o-hydroxyacetophenone, total recovery 90.2%, the ratio of o-hydroxyacetophenone are 80.5% (CN 1119639A).This method is with chlorobenzene or 1, and the 2-ethylene dichloride is a solvent, 60～90 ℃ of temperature of reaction, but used excessive greatly AlCl
3, the aftertreatment complexity, environmental pollution is serious.
Summary of the invention
The technical problem to be solved in the present invention provides a kind of preparation method to acetoxy acetophenone and adjacent acetoxy acetophenone.
Technical scheme of the present invention is: a kind of preparation method to acetoxy acetophenone and adjacent acetoxy acetophenone, it comprises the steps:
(1) adding Lewis acid and phenol in halogeno-benzene, is under 35～45 ℃ of conditions in temperature, and dripping acetyl chloride is under 50～55 ℃ of conditions in temperature, and stirring and refluxing 0.5～1 hour heats up 100～105 ℃ then, reacts 2～3 hours;
(2) reaction product in the step (1) is reduced to room temperature, be hydrolyzed with hydrochloric acid/ice, tell organic phase, freezing after-filtration obtains filter cake;
(3) with the filter cake recrystallization in water in the step (2), obtain parahydroxyacet-ophenone, the filtrate in the step (2) is carried out underpressure distillation, obtain o-hydroxyacetophenone;
(4) be under 40～50 ℃ of conditions with parahydroxyacet-ophenone in the step (3) and diacetyl oxide in temperature, add the pyridine of catalytic amount, reacted 1～3 hour, reaction finishes back recrystallization in hexanaphthene and obtains product to acetoxy acetophenone;
(5) be under 40～50 ℃ of conditions with o-hydroxyacetophenone in the step (3) and diacetyl oxide in temperature, add the vitriol oil of catalytic amount, reacted 1～3 hour, reaction finishes afterreaction liquid and washes with water, obtains the adjacent acetoxy acetophenone of product with 95% ethyl alcohol recrystallization again.
Halogeno-benzene is any one in chlorobenzene or the dichlorobenzene in the described step (1).
Lewis acid is ZnCl in the described step (1)
2Or AlCl
3In any one.
The invention has the beneficial effects as follows: the present invention adopts cost of material lower, the experiment condition gentleness, and the by product that produces in the experiment is few, and yield is higher, and the excellent popularization using value is arranged.
Description of drawings
Fig. 1 is the infrared spectrum characterization of adjacent acetoxy acetophenone;
Fig. 2 is that the ultra-violet absorption spectrum of adjacent acetoxy acetophenone characterizes;
Fig. 3 is the infrared spectrum characterization to acetoxy acetophenone;
Fig. 4 is the ultra-violet absorption spectrum sign to acetoxy acetophenone.
Embodiment
(1) preparation of parahydroxyacet-ophenone and o-hydroxyacetophenone
After 94.0g phenol and 100mL chlorobenzene mixed, under agitation condition, be added dropwise in the mixture of the aluminum trichloride (anhydrous) of 136g and 50mL chlorobenzene, the control rate of addition makes and reacts on 25 ℃ and carry out, and hydrogen chloride gas absorbs with water.35 ℃ of hierarchy of control temperature slowly drip as the 79mL Acetyl Chloride 98Min..After dripping end, be heated to 50 ℃ of stirring and refluxing 0.5 hour, then in 105 ℃ of reactions 2 hours.After reducing to room temperature,, tell lower floor's organic phase with the hydrolysis in 1: 4 of 400mL hydrochloric acid dilute solution/frozen water, washing, freezing, filter, with a little cold solvent washing leaching cake, drain, get thick product parahydroxyacet-ophenone.Crude product is with the water recrystallization, and activated carbon decolorizing gets white, needle-shaped crystals parahydroxyacet-ophenone 30.2g, 108～110 ℃ of fusing points, yield 22.2%.
Gained filtrate is carried out wet distillation, and the organic phase of telling is carried out fractionation, first distillating recovering solvent after drying, decompression rectifying down then, collect 101～105 ℃/2000Pa cut and get light yellow transparent liquid o-hydroxyacetophenone 92.5g, yield 68.0%, overall yield 90.2% (in phenol).
(2) preparation of adjacent acetoxy acetophenone
10mL o-hydroxyacetophenone and 10mL diacetyl oxide are mixed in flask, add the vitriol oil of catalytic amount, exothermic heat of reaction, 45 ℃ of hierarchy of control temperature, TLC monitoring reaction process.Reaction is reduced to room temperature after finishing.Reaction solution washes with water, removes the acetate of generation, leaves standstill, and filters, and the filter cake washing gets light yellow solid.Get the adjacent acetoxy acetophenone of white crystals, yield 92.7% (in o-hydroxyacetophenone) with 95% ethyl alcohol recrystallization.
(3) to the preparation of acetoxy acetophenone
5.6g parahydroxyacet-ophenone and 6mL diacetyl oxide are stirred to dissolving fully under the room temperature in flask.Heating in water bath to 45 ℃ adds the pyridine of catalytic amount, and solution is by the light yellow light green that becomes, TLC monitoring reaction process.After reaction finishes, with the shrend reaction of going out.The reaction solution of gained adds an amount of water.Leave standstill, separate out white crystals.Suction filtration, crude product gets the white crystals body to acetoxy acetophenone with the hexanaphthene recrystallization, yield 94.6% (in parahydroxyacet-ophenone).
Embodiment 2
(1) preparation of parahydroxyacet-ophenone and o-hydroxyacetophenone
After 94.0g phenol and 100mL dichlorobenzene mixed, under agitation condition, be added dropwise in the mixture of the Zinc Chloride Anhydrous of 136g and 50mL dichlorobenzene, the control rate of addition makes and reacts on 35 ℃ and carry out, and hydrogen chloride gas absorbs with water.45 ℃ of hierarchy of control temperature slowly drip as the 79mL Acetyl Chloride 98Min..After dripping end, be heated to 50 ℃ of stirring and refluxing 1 hour, then in 105 ℃ of reactions 3 hours.After reducing to room temperature,, tell lower floor's organic phase with the hydrolysis in 1: 4 of 400mL hydrochloric acid dilute solution/frozen water, washing, freezing, filter, with a little cold solvent washing leaching cake, drain, get thick product parahydroxyacet-ophenone.Crude product is with the water recrystallization, and activated carbon decolorizing gets white, needle-shaped crystals parahydroxyacet-ophenone 30.2g, 108～110 ℃ of fusing points, yield 22.2%.
Gained filtrate is carried out wet distillation, and the organic phase of telling is carried out fractionation, first distillating recovering solvent after drying, decompression rectifying down then, collect 101～105 ℃/2000Pa cut and get light yellow transparent liquid o-hydroxyacetophenone 92.5g, yield 68.0%, overall yield 90.2% (in phenol).
(2) preparation of adjacent acetoxy acetophenone
10mL o-hydroxyacetophenone and 10mL diacetyl oxide are mixed in flask, add the vitriol oil of catalytic amount, exothermic heat of reaction, 50 ℃ of hierarchy of control temperature, TLC monitoring reaction process.Reaction is reduced to room temperature after finishing.Reaction solution washes with water, removes the acetate of generation, leaves standstill, and filters, and the filter cake washing gets light yellow solid.Get the adjacent acetoxy acetophenone of white crystals, yield 92.7% (in o-hydroxyacetophenone) with 95% ethyl alcohol recrystallization.
(3) to the preparation of acetoxy acetophenone
5.6g parahydroxyacet-ophenone and 6mL diacetyl oxide are stirred to dissolving fully under the room temperature in flask.Heating in water bath to 40 ℃ adds the sodium acetate, anhydrous of catalytic amount, and solution is by the light yellow light green that becomes, TLC monitoring reaction process.After reaction finishes, with the shrend reaction of going out.The reaction solution of gained adds an amount of water.Leave standstill, separate out white crystals.Suction filtration, crude product gets the white crystals body to acetoxy acetophenone with the hexanaphthene recrystallization, yield 94.6% (in parahydroxyacet-ophenone).
(1) preparation of parahydroxyacet-ophenone and o-hydroxyacetophenone
After 94.0g phenol and 100mL chlorobenzene mixed, under agitation condition, be added dropwise in the mixture of the aluminum trichloride (anhydrous) of 136g and 50mL chlorobenzene, the control rate of addition makes and reacts on 30 ℃ and carry out, and hydrogen chloride gas absorbs with water.40 ℃ of hierarchy of control temperature slowly drip as the 79mL Acetyl Chloride 98Min..After dripping end, be heated to 50 ℃ of stirring and refluxing 0.5 hour, then in 105 ℃ of reactions 2 hours.After reducing to room temperature,, tell lower floor's organic phase with the hydrolysis in 1: 4 of 400mL hydrochloric acid dilute solution/frozen water, washing, freezing, filter, with a little cold solvent washing leaching cake, drain, get thick product parahydroxyacet-ophenone.Crude product is with the water recrystallization, and activated carbon decolorizing gets white, needle-shaped crystals parahydroxyacet-ophenone 30.2g, 108～110 ℃ of fusing points, yield 22.2%.
Gained filtrate is carried out wet distillation, and the organic phase of telling is carried out fractionation, first distillating recovering solvent after drying, decompression rectifying down then, collect 101～105 ℃/2000Pa cut and get light yellow transparent liquid o-hydroxyacetophenone 92.5g, yield 68.0%, overall yield 90.2% (in phenol).
(2) preparation of adjacent acetoxy acetophenone
10mL o-hydroxyacetophenone and 10mL diacetyl oxide are mixed in flask, add the vitriol oil of catalytic amount, exothermic heat of reaction, 40 ℃ of hierarchy of control temperature, TLC monitoring reaction process.Reaction is reduced to room temperature after finishing.Reaction solution washes with water, removes the acetate of generation, leaves standstill, and filters, and the filter cake washing gets light yellow solid.Get the adjacent acetoxy acetophenone of white crystals, yield 92.7% (in o-hydroxyacetophenone) with 95% ethyl alcohol recrystallization.
(3) to the preparation of acetoxy acetophenone
5.6g parahydroxyacet-ophenone and 6mL diacetyl oxide are stirred to dissolving fully under the room temperature in flask.Heating in water bath to 40 ℃ adds the pyridine of catalytic amount, and solution is by the light yellow light green that becomes, TLC monitoring reaction process.After reaction finishes, with the shrend reaction of going out.The reaction solution of gained adds an amount of water.Leave standstill, separate out white crystals.Suction filtration, crude product gets the white crystals body to acetoxy acetophenone with the hexanaphthene recrystallization, yield 94.6% (in parahydroxyacet-ophenone).
In the foregoing description, Perkin-Elmer 782 type Fourier infrared spectrographs, U.S. PE company; T6 new millennium ultraviolet spectrophotometer, Beijing is general analyse general.
The mechanism of the inventive method is as follows:
Acetyl Chloride 98Min. and AlCl
3The ethanoyl carbonium ion that effect forms generates mixture with phenyl ring generation electrophilic substitution reaction, obtains parahydroxyacet-ophenone and o-hydroxyacetophenone through hydrolysis.
With the vitriol oil/sodium-acetate/pyridine is catalyzer, with the ethanoyl carbonium ion of diacetyl oxide formation and the phenolic hydroxyl group effect of parahydroxyacet-ophenone and o-hydroxyacetophenone, generates respectively acetoxy acetophenone and adjacent acetoxy acetophenone.For example, be that the reaction mechanism of catalyzer is as follows with the pyridine:
Product is determined with ultra-violet absorption spectrum and infrared absorption spectrum the structure of acetoxy acetophenone and adjacent acetoxy acetophenone.
(1) infrared spectrum characterization of adjacent acetoxy acetophenone
Method: KBr compressing tablet
Ir data is as follows:
IR(KBr，cm
-1)：3069(w)，2926(s)，1756(s)，1684(s)，1603(m)，1575(w)，1483(m)，1452(m)，1369(s)，1302(w)，1286(w)，1250(m)，1219(s)，1197(s)，1166(m)，1127(w)，1072(m)，1039(w)，1007(m)，963(w)，956(m)，916(m)，827(m)，770(m)，743(w)，709(w)，657(w)，611(w)，602(w)，583(w)，550(w)，509(w)，494(w)。
Adjacent acetoxy acetophenone infrared spectra is resolved:
3069 (w) are aromatic ring C-H stretching vibration, 2926 (s) are that methyl C-H stretching vibration absorbs, 1756 (s) are ester carbonyl group C=O stretching vibration absorption peak, 1684 (s) are that ketone carbonyl C=O stretching vibration absorbs, 1603 (m), 1484 (m) and 1452 (m) are phenyl ring skeleton C=C stretching vibration absorption peak, 1369 (s) are methyl C-H symmetric curvature absorption of vibrations, 1219 (s) absorb for the acetate group stretching vibration, 1197 (s) are that phenyl ring C-O asymmetrical stretching vibration absorbs, 770 (m) ownership absorbs for C-H out-of-plane deformation vibration on the adjacent two replacement back aromatic rings on the phenyl ring, this absorption peak is on the phenyl ring 1, the adjacent dibasic charateristic avsorption band of 2-.
(2) ultra-violet absorption spectrum of adjacent acetoxy acetophenone characterizes
Solvent: methyl alcohol
Spectrum analysis: adjacent acetoxy acetophenone uv-absorbing wavelength theoretical value is 237nm, measured value 236nm.The transition of electron type is π-π
*(R absorption band).
(3) to the infrared spectrum characterization of acetoxy acetophenone
Method: KBr compressing tablet
Ir data is as follows:
IR(KBr，cm
-1)：3103(w)，3073(w)，3001(w)，2925(w)，1754(s)，1675(s)，1629(w)，1597(s)，1504(m)，1414(m)，1358(s)，1299(m)，1271(s)，1217(s)，1169(s)，1107(m)，1015(m)，962(m)，916(s)，855(m)，804(m)，626(m)，592(m)，561(w)，495(w)。
The acetoxy acetophenone infrared spectra is resolved:
3073 (w) and 3001 (w) are that unsaturated C-H stretching vibration absorbs on the phenyl ring, 2925 (w) are saturated C-H stretching vibration, 1754 (s) are ester carbonyl group C=O stretching vibration, 1675 (s) are ketone carbonyl C=O stretching vibration, 1597 (s), 1589 (m) and 1504 (m) are that phenyl ring skeleton C=C stretching vibration absorbs, 1358 (s) are methyl C-H symmetric curvature absorption of vibrations, 855 (m) ownership is on the phenyl ring 1,4-two replaces back C-H out-of-plane deformation vibration and absorbs, this peak is on the phenyl ring 1, the dibasic charateristic avsorption band of 4-.
(4) ultra-violet absorption spectrum to acetoxy acetophenone characterizes
Solvent: hexanaphthene
Spectrum analysis: to acetoxy acetophenone uv-absorbing wavelength theoretical value is 246nm, measured value 247nm.The transition of electron type is π-π
*(R absorption band).
Claims (4)
1. the preparation method to acetoxy acetophenone and adjacent acetoxy acetophenone is characterized in that it comprises the steps:
(1) adding Lewis acid and phenol in halogeno-benzene, is under 35～45 ℃ of conditions in temperature, and dripping acetyl chloride is under 50～55 ℃ of conditions in temperature, and stirring and refluxing 0.5～1 hour heats up 100～105 ℃ then, reacts 2～3 hours;
(2) reaction product in the step (1) is reduced to room temperature, be hydrolyzed with hydrochloric acid/ice solution, tell organic phase, freezing after-filtration obtains filter cake;
(3) with the filter cake recrystallization in water in the step (2), obtain parahydroxyacet-ophenone, the filtrate in the step (2) is carried out underpressure distillation, obtain o-hydroxyacetophenone;
(4) be under 40～50 ℃ of conditions with parahydroxyacet-ophenone in the step (3) and diacetyl oxide in temperature, add the pyridine of catalytic amount, reacted 1～3 hour, reaction finishes back recrystallization in hexanaphthene and obtains product to acetoxy acetophenone;
(5) be under 40～50 ℃ of conditions with o-hydroxyacetophenone in the step (3) and diacetyl oxide in temperature, add the vitriol oil of catalytic amount, reacted 1～3 hour, reaction finishes afterreaction liquid and washes with water, obtains the adjacent acetoxy acetophenone of product with 95% ethyl alcohol recrystallization again.
2. the preparation method to acetoxy acetophenone and adjacent acetoxy acetophenone according to claim 1 is characterized in that: halogeno-benzene is any one in chlorobenzene or the dichlorobenzene in the described step (1).
3. the preparation method to acetoxy acetophenone and adjacent acetoxy acetophenone according to claim 1 is characterized in that: Lewis acid is ZnCl in the described step (1)
2Or AlCl
3In any one.
4. the preparation method to acetoxy acetophenone and adjacent acetoxy acetophenone according to claim 1 is characterized in that: the pyridine of catalytic amount also can be the sodium acetate, anhydrous of catalytic amount in the described step (4).
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104529726A (en) * | 2014-12-16 | 2015-04-22 | 上海应用技术学院 | Preparation method of hydroxyacetophenone |
| CN104981452A (en) * | 2013-09-10 | 2015-10-14 | Rns株式会社 | Skin whitening agent containing novel cyclic compound |
| CN106916060A (en) * | 2017-02-22 | 2017-07-04 | 江苏新瀚新材料股份有限公司 | A kind of preparation method of high-purity parahydroxyacet-ophenone |
| CN109384657A (en) * | 2018-12-18 | 2019-02-26 | 苏州开元民生科技股份有限公司 | A kind of parahydroxyacet-ophenone synthetic method |
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| US4508924A (en) * | 1981-03-04 | 1985-04-02 | Basf Aktiengesellschaft | Preparation of o-acylphenols and p-acylphenols |
| CN1039412A (en) * | 1988-07-19 | 1990-02-07 | 赫希斯特人造丝公司 | The solvent-free hydrogenation of 4-acetoxyl methyl phenyl ketone prepares 4-acetoxystyrene and polymkeric substance and hydrolysate |
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2009
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| US4508924A (en) * | 1981-03-04 | 1985-04-02 | Basf Aktiengesellschaft | Preparation of o-acylphenols and p-acylphenols |
| CN1039412A (en) * | 1988-07-19 | 1990-02-07 | 赫希斯特人造丝公司 | The solvent-free hydrogenation of 4-acetoxyl methyl phenyl ketone prepares 4-acetoxystyrene and polymkeric substance and hydrolysate |
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| B.B.CORSON等: "Preparation of Vinylphenols and Isopropenylphenols", 《J. ORG.CHEM》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104981452A (en) * | 2013-09-10 | 2015-10-14 | Rns株式会社 | Skin whitening agent containing novel cyclic compound |
| CN104529726A (en) * | 2014-12-16 | 2015-04-22 | 上海应用技术学院 | Preparation method of hydroxyacetophenone |
| CN106916060A (en) * | 2017-02-22 | 2017-07-04 | 江苏新瀚新材料股份有限公司 | A kind of preparation method of high-purity parahydroxyacet-ophenone |
| CN106916060B (en) * | 2017-02-22 | 2020-07-24 | 江苏新瀚新材料股份有限公司 | Preparation method of high-purity p-hydroxyacetophenone |
| CN109384657A (en) * | 2018-12-18 | 2019-02-26 | 苏州开元民生科技股份有限公司 | A kind of parahydroxyacet-ophenone synthetic method |
| CN109384657B (en) * | 2018-12-18 | 2021-08-31 | 苏州开元民生科技股份有限公司 | Synthetic method of p-hydroxyacetophenone |
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Application publication date: 20110615 |