Potassium Hydroxide → 2-(4-Bromophenyl)-2-methylpropanoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-(4-bromophenyl)-2,2-dimethylacetate (3880 μL, 15090 μmol) in EtOH (80 mL) and water (20 mL) was treated with KOH (4233 mg, 75450 μmol). The reaction was heated to 90° C. After 15 hours, the reaction was cooled to 23° C. and concentrated in vacuo. The crude mixture was partitioned between water/diethyl ether (150 mL each). The aqueous layer was separated and extracted with diethyl ether (100 mL). The combined ether layers were then extracted with a 1N NaOH solution (25 mL). The combined aqueous washes were acidified with concentrated HCl to pH=2.0 and extracted with EtOAc (3×100 mL). The combined EtOAc layers were dried over MgSO4, and concentrated in vacuo to afford 3144 mg of 2-(4-bromophenyl)-2-methylpropanoic acid.

Provenance & Evidence