Ethanol → 4-Methoxy-gamma,gamma,3-trimethylbenzenebutanoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-methoxy-3-methylphenyl)-4-methyl-pentanoic acid ethyl ester (Compound 4, 6.8 g, 25.8 mmol) and 20 mL of absolute ethyl alcohol was added aqueous 5 M KOH (6 mL). The resulting solution was heated in an 60° C. bath for 24 h. The solution was cooled to room temperature, diluted with water and washed once with 2:1 hexane:ethyl acetate solution, and the layers were separated. The aqueous layer was acidified with HCl 2 N to pH=0-1 and the product extracted three times with ethyl acetate. The combined organic extracts were washed with brine, and dried over MgSO4, and filtered. The solvent was removed to give 5.9 g (97%) of the title compound as a dark oil.

Provenance & Evidence