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Title: An efficient method for synthesis of 2-ethyl hexyl-4-methoxy cinnamate: A raw material for cosmetic industry
Authors: Yadav, Vasanti G
Chandalia, S B
Issue Date: Jan-1999
Publisher: NISCAIR-CSIR, India
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/methyl 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.
Page(s): 19-23
ISSN: 0975-0991 (Online); 0971-457X (Print)
Appears in Collections:IJCT Vol.06(1) [January 1999]

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