Potassium Hydroxide → HCID 66616530, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of dimethyl 5-cyclopropylisophthalate (0.8 g, 3.42 mmol) in MeOH (10 mL) and THF (10 mL) was added potassium hydroxide (0.23 g, 4.1 mmol) with stirring. The reaction mixture was heated at 78° C. for 7 h. It was cooled to rt and concentrated in vacuo. To the residue was added a small amount of acetic acid. The mixture was purified by preparative HPLC. The fractions containing the desired product were combined, concentrated and lyophilized to afford 5-cyclopropylisophthalic acid as a white solid (89 mg, 12%) and 3-cyclopropyl-5-(methoxycarbonyl)benzoic acid as a white solid (0.43 g, 56%). 1H NMR (DMSO-d6): δ 13.21 (s, 2H), 8.25 (t, J=1.2 Hz, 1H), 7.85 (d, J=1.2 Hz, 2H), 2.13 (m, 1H), 1.03 (m, 2H), 0.76 (m, 2H).

Provenance & Evidence