[1,1';3',1'']Terphenyl-2'-yl-acetonitrile → 1,1':3',1''-Terphenyl-2'-ylacetic acid

Participants

Reaction Steps

A mixture of [1,1′;3′,1″]terphenyl-2′-yl-acetonitrile (0.78 g, 2.9 mmol) in 28 mL of 10:3:1 acetic acid/sulfuric acid/water was refluxed for 2 days The reaction mixture was cooled and diluted with water. The aqueous was extracted with diethyl ether, dried over magnesium sulfate and concentrated to give 1,1′:3′,1″-terphenyl-2′-ylacetic acid as a tan solid (0.64 g, 76%): MS (ESI) m/z 287.1 (M−H); MS (ESI) m/z 575.2 (2M−H); MS (ESI) m/z 333 (M+FA−H); HRMS calcd for C20H16O2, 288.1150. Found (ESI+), 289.12244; 1H NMR (DMSO-d6): δ 3.30 (s, 2H), 7.30-7.50 (m, 13H), 12.07 (br s, 1H); Anal. Calcd for C20H16O2: C, 83.31; H, 5.59. Found: C, 83.02; H, 5.35.

Provenance & Evidence