Hydrochloric Acid → 3-(1,1-Dimethyl-2-oxoethyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(1-cyano-1-methylethyl)benzoic acid (8.60 g, 45.5 mmol) in toluene (60 mL)/tetrahydrofuran (40 mL) was added dropwise 1.0 M hexane solution (100 mL, 100 mmol) of diisobutylaluminum hydride at −78° C. over 1 hr. After the completion of the dropwise addition, the mixture was stirred at −78° C. for 1 hr and at 0° C. for 1 hr. The reaction mixture was poured into a mixture of ethyl acetate (200 mL) and 3N hydrochloric acid (300 mL), and the organic layer was separated from the aqueous layer. The aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layer was washed with saturated brine (50 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was crystallized from ethyl acetate/hexane to give the title compound (6.39 g, 73%) as colorless crystals.

Provenance & Evidence