JPS5695142A - Preparation of aliphatic aldehyde - Google Patents
Preparation of aliphatic aldehydeInfo
- Publication number
- JPS5695142A JPS5695142A JP17029779A JP17029779A JPS5695142A JP S5695142 A JPS5695142 A JP S5695142A JP 17029779 A JP17029779 A JP 17029779A JP 17029779 A JP17029779 A JP 17029779A JP S5695142 A JPS5695142 A JP S5695142A
- Authority
- JP
- Japan
- Prior art keywords
- acetal
- formula
- compound
- alkyl
- removal reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 aliphatic aldehyde Chemical class 0.000 title abstract 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 5
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE: To prepare the titled compound useful for the synthesis of perfumery, pesticides, pharmaceuticals, etc., under mild conditions, in high purity and yield, without using expensive raw materials, by the acetal removal reaction of an easily available acetal compound as a starting material.
CONSTITUTION: An acetal of formula I [R1 is 1W20C alkyl, 2W20C alkenyl or 2W20C alkynyl; R2 is 1W5C alkyl, benzyl, or two R2 together form (CH2)n; n is 2 or 3] is subjected to acetal removal reaction in the presence of an acidic catalyst such as sulfuric acid, formic acid, etc. in a solvent such as water, acetone, etc., pref. at about -10W+80°C to obtain the compound of formula II. The starting compound of formula I can be prepared easily by coupling a β-halopropanal acetal of formula III (X is Br or I) with a Grignard reagent of formula IV (Y is halogen) in an inert organic solvent in the presence of a coupling catalyst.
COPYRIGHT: (C)1981,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17029779A JPS5695142A (en) | 1979-12-28 | 1979-12-28 | Preparation of aliphatic aldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17029779A JPS5695142A (en) | 1979-12-28 | 1979-12-28 | Preparation of aliphatic aldehyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5695142A true JPS5695142A (en) | 1981-08-01 |
| JPS6113696B2 JPS6113696B2 (en) | 1986-04-15 |
Family
ID=15902344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17029779A Granted JPS5695142A (en) | 1979-12-28 | 1979-12-28 | Preparation of aliphatic aldehyde |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5695142A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5925347A (en) * | 1982-08-03 | 1984-02-09 | T Hasegawa Co Ltd | Preparation of 1,1-dialkoxy-3-alkynes |
| US4933500A (en) * | 1988-05-16 | 1990-06-12 | Rhone-Poulenc Sante | Process for the preparation of citral |
| JP2005538224A (en) * | 2002-09-09 | 2005-12-15 | ネクター セラピューティックス エイエル，コーポレイション | Water-soluble polymer alkanal |
| WO2006083030A1 (en) * | 2005-02-04 | 2006-08-10 | Ajinomoto Co., Inc. | Process for producing fatty acid and salt or crystal of fatty acid |
| JP2010523615A (en) * | 2007-04-11 | 2010-07-15 | クラリアント・スペシャルティ・ファイン・ケミカルズ（フランス） | Deacetalization of α-aminoacetals |
| CN104710293A (en) * | 2013-12-13 | 2015-06-17 | 上海生华化学科技有限公司 | New method for synthesizing dialdehyde compound |
| JP2017155013A (en) * | 2016-03-03 | 2017-09-07 | 信越化学工業株式会社 | Terminal conjugated trienal acetal compound |
-
1979
- 1979-12-28 JP JP17029779A patent/JPS5695142A/en active Granted
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5925347A (en) * | 1982-08-03 | 1984-02-09 | T Hasegawa Co Ltd | Preparation of 1,1-dialkoxy-3-alkynes |
| US4933500A (en) * | 1988-05-16 | 1990-06-12 | Rhone-Poulenc Sante | Process for the preparation of citral |
| JP2005538224A (en) * | 2002-09-09 | 2005-12-15 | ネクター セラピューティックス エイエル，コーポレイション | Water-soluble polymer alkanal |
| US7838595B2 (en) | 2002-09-09 | 2010-11-23 | Nektar Therapeutics | Water-soluble polymer alkanals |
| JP4764630B2 (en) * | 2002-09-09 | 2011-09-07 | ネクター セラピューティックス | Water-soluble polymer alkanal |
| US8076412B2 (en) | 2002-09-09 | 2011-12-13 | Nektar Therapeutics | Water-soluble polymer alkanals |
| US8853325B2 (en) | 2002-09-09 | 2014-10-07 | Nektar Therapeutics | Water-soluble polymer alkanals |
| WO2006083030A1 (en) * | 2005-02-04 | 2006-08-10 | Ajinomoto Co., Inc. | Process for producing fatty acid and salt or crystal of fatty acid |
| JP2010523615A (en) * | 2007-04-11 | 2010-07-15 | クラリアント・スペシャルティ・ファイン・ケミカルズ（フランス） | Deacetalization of α-aminoacetals |
| CN104710293A (en) * | 2013-12-13 | 2015-06-17 | 上海生华化学科技有限公司 | New method for synthesizing dialdehyde compound |
| CN104710293B (en) * | 2013-12-13 | 2020-07-14 | 上海生华化学科技有限公司 | Novel method for synthesizing dialdehyde compound |
| JP2017155013A (en) * | 2016-03-03 | 2017-09-07 | 信越化学工業株式会社 | Terminal conjugated trienal acetal compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6113696B2 (en) | 1986-04-15 |
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