Hydrochloric Acid → 2,2'-Dimethyl-[1,1'-biphenyl]-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2,2′-dimethyl-1,1′-biphenyl-4-carboxylate of Step A (24.7 g, 103 mmol) in 5:1 tetrahydrofuran:methanol (200 mL) was added 1 M aqueous sodium hydroxide (108 mL, 108 mmol). The reaction mixture heated at reflux for 1 hour, cooled and then concentrated in vacuo to remove organic solvents. The resulting aqueous solution was cooled to 0° C. and 2 M aqueous hydrochloric acid (60 mL, 120 mmol) added slowly followed by water (60 mL) to facilitate stirring of the precipitated product. The suspension was stirred for 1 h at 0° C. then filtered to afford the title compound (22.6 g) as a white solid, m. p. 140-143° C.

Provenance & Evidence