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Process for the preparation of beta-ionylideneacetaldehyde

A technology of fenugreek and acetaldehyde, which is applied in the field of β-galenylidene acetaldehyde, can solve the problems of unsuitable and expensive

Inactive Publication Date: 2005-05-04
RANBAXY LAB LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method is also unsuitable from a commercial point of view as it requires many steps to produce trans-β-galenylidene-acetaldehyde and requires the use of expensive triiron dodecacarbonyl

Method used

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  • Process for the preparation of beta-ionylideneacetaldehyde
  • Process for the preparation of beta-ionylideneacetaldehyde
  • Process for the preparation of beta-ionylideneacetaldehyde

Examples

Experimental program
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Embodiment

[0035] Preparation of β-zhixiang subunit acetaldehyde (I)

[0036] Step a) Preparation of ethyl β-zhixiangylidene acetate (IV)

[0037] A toluene (1 liter) solution of triethyl phosphonoacetate (1.40 kg) was added to a mixture of sodium amide (0.236 kg) and toluene (6.5 liters) while stirring at about 40°C under nitrogen. The reaction mixture was stirred at 40-45°C for 6 hours, cooled to 0-5°C, and a toluene (1.5 liter) solution of β-genyl and ionone (1 kg) was slowly added at 0-10°C. The reaction mixture was stirred at 65°C for 15 hours and cooled to 20-25°C. Water (4 liters) was added to the reaction mixture and then stirred for another 15 minutes. The toluene layer was separated and distilled under vacuum at 60-80°C to obtain the title compound of formula IV with a yield of 87%, which was a mixture of 9-cis and 9-trans isomers in a ratio of 1:7.

[0038] Step b) Preparation of β-zhixiang subunit ethanol (V)

[0039] Under nitrogen, lithium aluminum hydride (0.11 kg) was added t...

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Abstract

The present invention relates to an industrially advantageous method for producing β-Pyroxylin acetaldehyde of structural formula I, which is a key intermediate for synthesizing vitamin A and related compounds such as tretinoin and isotretinoin. These compounds have a wide range of biological activities. For example, isotretinoin can inhibit the function and keratinization of sebaceous glands and is used to treat skin diseases such as acne. Isotretinoin also has anticancer activity.

Description

Invention field [0001] The present invention relates to an industrially advantageous method for producing β-ionylideneacetaldehyde of structural formula I, [0002] [0003] Formula I [0004] β-Pycnidylacetaldehyde is a key intermediate for the synthesis of vitamin A and related compounds such as tretinoin and isotretinoin. These compounds have a wide range of biological activities. For example, isotretinoin can inhibit the function of sebaceous glands and keratinization and is used to treat skin diseases such as acne. Isotretinoin also has anti-cancer activity. Background of the invention [0005] Using β-pyogenol and ionone as starting materials, β-pyogenol acetaldehyde was synthesized. All the double bonds in β-pyrogylidene acetaldehyde have a trans configuration. The main synthetic difficulty is to maintain the conjugated trans-polyene system in the molecule. The following briefly describes the existing synthesis methods of β-zhixiang subunit acetaldehyde. [0006] J. Am. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/147C07C33/14C07C45/29C07C47/225C07C67/343C07C403/14
CPCC07B2200/09C07C29/147C07C33/14C07C67/343C07C403/08C07C403/14C07C403/20C07C2601/16C07C69/608
Inventor M·萨尔曼P·C·雷N·库马J·S·巴布
Owner RANBAXY LAB LTD
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