Potassium Hydroxide → HCID 22041394, compound

Participants

Reaction Steps

A mixture of 7-(5-Formyl-2-trifluoromethoxy-phenyl)-3,3-dimethyl-2,3-dihydro-benzofuran-5-carboxylic acid methyl ester (1.76 g, 4.82 mmol) (example 8) and 5N potassium hydroxide (2 mL) in methanol (20 mL) was heated at reflux for 1 hour. The solvent was then evaporated. The mixture was diluted with water and washed twice with diethyl ether. The aqueous layers were acidified with 1N HCl and extracted twice with ethyl acetate. The organic combined extract was further washed with water, brine, dried (MgSO4), filtered and evaporated. The residue was chromatographed on silica gel (30% ethyl acetate in hexane) to afford 112 mg of 7-(5-formyl-2-trifluoromethoxy-phenyl)-3,3-dimethyl-2,3-dihydro-benzofuran-5-carboxylic acid. 10% yield. 1H-NMR (300 MHz, CDCl3): 1.43 (s, 6H), 4.36 (s, 2H), 7.51 (d, J=8.2 Hz, 1H), 7.92–8.04 (m, 4H), 10.05 (s, 1H).

Provenance & Evidence