Hydrochloric Acid → 2-(2-Chlorophenyl)propanoic acid

Participants

Reaction Steps

A solution of diisopropylamine (1.6 mL, 12 mmole) in 20 mL of THF at −78° was treated with n-BuLi (7.5 mL of a 1.6N solution in hexane, 12 mmole). The solution was stirred 10 minutes, and then treated with HMPA (2.16 mL, 12 mmole), and stirred an additional 2 minutes. A solution of o-chlorophenylacetic acid (850 mg, 5 mmole) in 4 mL of THF was added, the reaction was warmed to 23°, stirred 45 minutes, warmed to 50° and stirred for 5 minutes, and then cooled to 0°. Mel (1 mL) was added, the reaction was warmed to 23°, and stirred for 30 minutes. The reaction was diluted with H2O, acidified with HCl, and extracted with Et2O. The extracts were washed with 0.1N HCl, H2O, aqueous NaHSO3, dried, and the solvent removed, and gave the titled compounds as a white crystalline solid, 603 mg (66% yield). MS (ESI) 185 (MH+).

Provenance & Evidence