Sulfuric Acid → 2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester

Participants

Reaction Steps

U.S. Pat. No. 5,527,947 describes a process in which C1-C4-alkoxybenzaldehydes, such as anisaldehyde, and C1-C4-alkyl acetates, such as methyl acetate, are dissolved in an inert hydrocarbon, such as heptane, toluene or petroleum ether. In the presence of a strongly alkaline metal base, such as sodium methoxide, the feed substances react to give a mixture of the corresponding C1-C4-alkyl-C1-C4-alkoxy cinnamates, the alkali metal salts of the corresponding C1-C4-alkoxy cinnamic acid and the C1-C4-alkanols. Following acidification of the reaction mixture with a strong polybasic acid, such as sulfuric acid, the liberated acetic acid is esterified with the C1-C4-alkanoles and distilled off. The mixture of C1-C4-alkyl-C1-C4-alkoxycinnamates and C1-C4-alkoxycinnamic acids which remains is reacted with a C5-C14-alkanol in the presence of a metal salt of a strong polybasic acid, such as sulfuric acid. Following transesterification and esterification, the corresponding C5-C14-alkyl-C1-C4-alkoxycinnamate, e.g. 2-ethylhexyl-4-methoxycinnamate, is obtained with 83 to 87% yield.

Provenance & Evidence