Ethanol → 3-(3,5-Di-tertiary-butyl-4-hydroxyanilino)phenoxyacetic acid

Participants

Reaction Steps

A mixture of 5.0 g of 3-(2,6-di-tertiary-butyl-cyclohexadienon-4-ylideneamino)phenoxyacetic acid, 250 ml of ethanol and 10 mg of 5% palladium on charcoal catalyst was placed on a Paar apparatus. Hydrogenation was complete after five hours. The reaction mixture was filtered to remove the catalyst and the filtrate was evaporated to give a thick brown oil. The oil was dissolved in 20 ml of benzene, filtered, diluted with 20 ml of cyclohexane and 10 ml of hexane, and chilled to give 1.4 g of light tan crystalline 3-(3,5-di-tertiary-butyl-4-hydroxyanilino)phenoxyacetic acid, m.p. 127°-127.5° C. Analysis: Calculated for C22H29NO4 ; % C, 71.1; % H, 7.9; % N, 3.8; Found: % C, 70.3; H, 7.6; % N, 3.7.

Provenance & Evidence