Ethyl 3-[3-(4-methylbenzoyl)phenyl]prop-2-enoate → Ethyl 3-[3-(4-methylbenzoyl)phenyl]propanoate

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Reaction Steps

Ethyl 3-(4-toluoyl)cinnamate (Example 4) (3.0 g), in solution in ethyl acetate (90 mL) was shaken with hydrogen in the presence of Raney nickel catalyst until slightly more than 1 molar equivalent of hydrogen had been absorbed. After removal of the catalyst by filtration, the residue was dissolved in dichloro-methane (200 mL), barium manganate (14 g) was added and the mixture was stirred at 50° for 2 hours. The filtered solution was evaporated to leave pure ethyl 3-(3-(4-toluoyl)phenyl)propionate as a yellow oil. (A portion hydrolysed with dilute aqueous alcoholic sodium hydroxide gave the corresponding carboxylic acid, m.p. 137°-138.5°).

Provenance & Evidence