Isopropanol → 2-(Propan-2-yloxy)-4-(trifluoromethyl)benzoic acid

Participants

Reaction Steps

To a solution of 500 mg (2.271 mmol) 2-hydroxy-4-trifluoromethyl-benzoic acid methyl ester (CAS: 345-28-8), 209 ul (2.725 mmol) 2-propanol and 706.2 mg (2.612 mmol) triphenylphosphine in 6.5 ml tetrahydrofuran under nitrogen at 0° C., was added dropwise a solution of 575.2 mg (2.498 mmol) di-tert-butyl azodicarboxylate in 1 ml tetrahydrofuran. The reaction mixture was allowed to warm to room temperature and stirred for 1.5 hours. 8 ml (15.9 mmol) 2N NaOH was added and the reaction mixture was warmed at 80° C. for 5 hours. The reaction mixture extracted twice with 5 ml ether. The aqueous layer was acidified under ice bath cooling with a 5N HCl solution to pH 1. The resulting precipitate was filtered and dried in vacuo to provide 444 mg (y: 78.8%) of the expected compound as a white solid. MS (m/e): 247.0 (MH+).

Provenance & Evidence