Hydrochloric Acid → 4-(4-Isopropylphenyl)butanoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of compound 76 (0.5 g, 2.27 mmol) and 2 mL of 80% hydrazine hydrate was stirred at 45° C. for 1 hour. To the mixture, KOH (1 g, 17.8 mmol) was added and the reaction mixture was heated to 104-150° C. for 2 hours. After cooling to ambient temperature, the reaction mixture was diluted with 10 mL of water and acidified to pH 2 with aqueous HCl (1 M) and extracted with ethyl acetate (2×20 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica-gel (2×15 cm, petroleum ether:ethyl acetate=8:1 elution) to give 275 mg of compound 77. MS m/z 207 (M+H)+.

Provenance & Evidence