CN104086378A - Preparation method of 2-(4-benzyloxyphenyl) ethanol - Google Patents
Preparation method of 2-(4-benzyloxyphenyl) ethanol Download PDFInfo
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- CN104086378A CN104086378A CN201410364003.3A CN201410364003A CN104086378A CN 104086378 A CN104086378 A CN 104086378A CN 201410364003 A CN201410364003 A CN 201410364003A CN 104086378 A CN104086378 A CN 104086378A
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- ethanol
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- benzyloxy phenyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/64—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring
- C07C37/66—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring by conversion of hydroxy groups to O-metal groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of 2-(4-benzyloxyphenyl) ethanol. The preparation method comprises the following steps: stirring p-hydroxyphenylethyl alcohol and water, uniformly mixing, and dropwise adding a sodium hydroxide aqueous solution to perform salt forming reaction to generate 4-hydroxyphenylethyl alcohol sodium salt; then performing vacuum reduced pressure distillation, adding toluene to reflux with water, and then dropwise adding benzyl chloride to perform reaction to generate a 2-(4-benzyloxyphenyl) ethanol crude product; and then standing, filtering, crystallizing and drying to obtain a fine product namely 2-(4-benzyloxyphenyl) ethanol. The preparation method disclosed by the invention is simple and easy to operate, and is less in product by-product and high in product yield; preferably, the product yield can reach 85%; and the preparation method can be used for reducing the production cost and improving the production efficiency at the same time.
Description
Technical field
The present invention relates to a kind of biological chemical field, relate in particular to the preparation method of a kind of 2-(4-benzyloxy phenyl) ethanol.
Background technology
2-(4-benzyloxy phenyl) ethanol molecule formula is C15H1602, is a kind of important organic chemistry product, is mainly used in the high-end Field of Fine Chemicals such as medicine, agricultural chemicals, novel material.Existing 2-(4-benzyloxy phenyl) ethanol preparation technology, the problem such as reaction scheme is long, and method is loaded down with trivial details, and by product is many, causes product yield low, and production efficiency is poor.
Therefore,, for addressing the above problem, spy provides a kind of new technical scheme.
Summary of the invention
The object of this invention is to provide a kind of yield high, cost is low, the preparation method of 2-simple to operate (4-benzyloxy phenyl) ethanol.
The present invention is achieved through the following technical solutions:
A preparation method for 2-(4-benzyloxy phenyl) ethanol, comprises the following steps:
A, in clean there-necked flask, add water and p-hydroxyphenylethanol, be uniformly mixed, then drip sodium hydroxide solution, time for adding is controlled at 1～3h, and reaction generates into 4-hydroxylphenylethyl alcohol sodium salt, and reaction equation is as follows:
B, dropwise after, underpressure distillation under 0.085MPa vacuum tightness, is down to normal temperature after stopping steaming and adds refluxing toluene band water, is warming up to reflux state, the band water that refluxes, to after anhydrous, keeps the 1～2h that refluxes;
C, by gained material cooling in step b, temperature is less than 30 ℃, then drips Benzyl Chloride, time for adding is controlled at 1～1.5h, is warming up to and refluxes 90～110 ℃, insulation reaction 25～30h after dropping, can obtain 2-(4-benzyloxy phenyl) ethanol crude product, reaction equation is as follows:
D, step c are after completion of the reaction, add toluene and water, stir cooling, standing 0.5h layering after 50～60 ℃ of stirring 0.5～1h of holding temperature, extracting organic layer is cooled to below 20 ℃, stirred crystallization 5～10h crystallization, then obtains 2-(4-benzyloxy phenyl) ethanol fine work through filtration drying.
The mass ratio of described hydroxylphenylethyl alcohol, sodium hydroxide and Benzyl Chloride is: 3: 1: 3.
Condition dry in described steps d is: temperature is 50～55 ℃ of dry 8～10h.
The invention has the beneficial effects as follows: the present invention is simple to operate, easy to operate, face and product by product are few, and product yield is high, preferably can reach 85%, has not only reduced production cost, has improved production efficiency simultaneously.
Embodiment
Below in conjunction with embodiment, a kind of 2-of the present invention (4-benzyloxy phenyl) ethanol preparation method is further illustrated.
Embodiment
In 1000ml there-necked flask, add 200ml water, 50g p-hydroxyphenylethanol, is uniformly mixed, and in room temperature, drips pre-configured sodium hydroxide solution (16.5g sodium hydroxide+50ml water), time for adding 2h; Dropwise, underpressure distillation under 0.085MPa vacuum tightness, approximately steams 200ml water left and right, stops steaming; Add 250ml refluxing toluene band water, be warming up to reflux state, the band water that refluxes, to anhydrous, be with water to finish and kept backflow 1.5h; Cooling, temperature are less than 30 ℃, start to drip 50g Benzyl Chloride, and time for adding is controlled at 1h; Dropwise, be warming up to and reflux 100 ℃, insulation reaction 25h; Reaction is finished, add 200 toluene, 200ml water, stirs cooling, standing 0.5h layering after 55 ℃ of stirring 0.5h of holding temperature, extracting organic layer is cooled to below 20 ℃, low rate mixing crystallization 8h crystallization, suction filtration obtains wet product, through 50 ℃ of dry 9h, obtain product 2-(4-benzyloxy phenyl) ethanol 63.5g, yield 76.8%.
The above, be only a wherein embodiment of invention, is not the present invention to be done to the restriction of any other form, and according to any modification or equivalent variations that technical spirit of the present invention is done, still belong to invention scope required for protection.
Claims (3)
1. a preparation method for 2-(4-benzyloxy phenyl) ethanol, is characterized in that: comprise the following steps:
A, in clean there-necked flask, add water and p-hydroxyphenylethanol, be uniformly mixed, then drip oxygen sodium hydroxide solution, time for adding is controlled at 1～3h, and reaction generates into 4-hydroxylphenylethyl alcohol sodium salt, and reaction equation is as follows:
B, dropwise after, underpressure distillation under 0.085MPa vacuum tightness, is down to normal temperature after stopping steaming and adds refluxing toluene band water, is warming up to reflux state, the band water that refluxes, to after anhydrous, keeps the 1～2h that refluxes;
C, by gained material cooling in step b, temperature is less than 30 ℃, then drips Benzyl Chloride, time for adding is controlled at 1～1.5h, is warming up to and refluxes 90～110 ℃, insulation reaction 25～30h after dropping, can obtain 2-(4-benzyloxy phenyl) ethanol crude product, reaction equation is as follows:
D, step c are after completion of the reaction, add toluene and water, stir cooling, standing 0.5h layering after 50～60 ℃ of stirring 0.5～1h of holding temperature, extracting organic layer is cooled to below 20 ℃, stirred crystallization 5～10h crystallization, then obtains 2-(4-benzyloxy phenyl) ethanol fine work through filtration drying.
2. the preparation method of a kind of 2-(4-benzyloxy phenyl) ethanol according to claim 1, is characterized in that: the mass ratio of described hydroxylphenylethyl alcohol, sodium hydroxide and Benzyl Chloride is: 3: 1: 3.
3. the preparation method of a kind of 2-(4-benzyloxy phenyl) ethanol according to claim 1, is characterized in that: condition dry in described steps d is: temperature is 50～55 ℃ of dry 8～10h.
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| CN201410364003.3A CN104086378A (en) | 2014-07-25 | 2014-07-25 | Preparation method of 2-(4-benzyloxyphenyl) ethanol |
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| CN201410364003.3A CN104086378A (en) | 2014-07-25 | 2014-07-25 | Preparation method of 2-(4-benzyloxyphenyl) ethanol |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106518630A (en) * | 2015-09-10 | 2017-03-22 | 江苏扬农化工股份有限公司 | Method for synthesizing 6-chloro-2-methoxytoluene |
| CN114213248A (en) * | 2021-12-08 | 2022-03-22 | 郑州睿嘉纳米新材料科技有限公司 | Preparation method of 4-benzyloxy phenyl ethyl n-decanoate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102898289A (en) * | 2012-10-11 | 2013-01-30 | 江苏德峰药业有限公司 | Method for synthesizing 2-(4-benzylmethoxyphenyl)ethanol medical intermediate |
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2014
- 2014-07-25 CN CN201410364003.3A patent/CN104086378A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102898289A (en) * | 2012-10-11 | 2013-01-30 | 江苏德峰药业有限公司 | Method for synthesizing 2-(4-benzylmethoxyphenyl)ethanol medical intermediate |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106518630A (en) * | 2015-09-10 | 2017-03-22 | 江苏扬农化工股份有限公司 | Method for synthesizing 6-chloro-2-methoxytoluene |
| CN106518630B (en) * | 2015-09-10 | 2019-04-19 | 江苏扬农化工股份有限公司 | A method of the synthesis chloro- 2- methoxy toluene of 6- |
| CN114213248A (en) * | 2021-12-08 | 2022-03-22 | 郑州睿嘉纳米新材料科技有限公司 | Preparation method of 4-benzyloxy phenyl ethyl n-decanoate |
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Application publication date: 20141008 |