An efficient method for synthesis of 2-ethyl hexyl-4-methoxy cinnamate: A raw material for cosmetic industry
Year: 1999
Type: article
Abstract: Methyl, ethyl and isopropyl esters of 4-methoxy cinnamic acid could be synthesized by Claisen condensation of anisaldehyde with the respective alkyl acetate at a temperature of 0 - 5°C using stoichiometric amount of sodium and a few drops of methanol, the latter being used as an initiator. The yield of the ester of cinnamic acid was about 77%. When the reaction was extended to the synthesis of 2-ethylhexyl ester of cinnamic acid, the reaction rates were rather very poor and it was necessary to carry out the reaction at the temperature of 28°C which resulted in the extensive hydrolysis of the starting acetate and the product ester. In the case of 2-ethyl hexyl ester, therefore, it may be desirable to resort to the synthesis of ethyl / methyl ester of the cinnamic acid by Claisen condensation followed by transesterification of the ethyl / methy ester. Thus, transesterification of ethyl 4-methoxy cinnamate with excess of 2-ethyl hexanol and p-toluenesulfonic acid as catalyst at 150°C gave a yield of 93% in 6 h.
Authors: Vasanti G. Yadav, S. B. Chandalia
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W2416316282