Process for producing 2-ethylhexyl-p-methoxycinnamate

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

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560 55, C07C 6976

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active

049703323

ABSTRACT:
A process for producing cinnamates comprising reacting an iodobenzene compound with an acrylate ester in the presence of trialkylamine and a catalyst comprising palladium on a support. In one embodiment, 2-ethylhexyl-p-methoxycinnamate is produced by the process comprising diazotizing p-anisidine to produce a diazotization product and reacting the diazotization product with an aqueous iodide solution to produce 4-iodoanisole, reacting the 4-iodoanisole product with 2-ethylhexylacrylate in the presence of trialkylamine and a catalyst comprising palladium on a support to produce 2-ethylhexyl-p-methoxycinnamate and a trialkylamine-hydroiodide salt and then recovering iodide and trialkylamine from the trialkylamine-hydroiodide salt by reacting the salt with an alkali hydroxide.

REFERENCES:
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patent: 3705919 (1972-12-01), Heck
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patent: 4592906 (1986-06-01), Baker
patent: 4618698 (1986-10-01), Beitzke
patent: 4620027 (1986-10-01), Hsu
patent: 4737591 (1988-04-01), Hsu
Heck, et al., J. Org. Chem., 37(14):2320 (1972).
Patel, et al., J. Org. Chem., 42(24):3903 (1977).
Mori, et al., Bull. Chem. Soc. of Japan, 46:1505-1508 (1973).

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