Ethanol → 4-(1-Cyclohexen-1-yl)-3-ethylbenzoic acid

Participants

Reaction Steps

4-(1-cyclohexen-1-yl)-3-ethylbenzonitrile (D17) (824 mg, 3.91 mmol) and potassium hydroxide (2.19 g, 39.1 mmol) in ethanol (36 mL) and water (8 mL) were heated at 90° C. (block temperature) for 20 h. The reaction mixture was concentrated in vacuo and the residue partitioned between ethyl acetate (120 mL) and aqueous hydrochloric acid (2M, 50 mL) before the organic phase was washed with further hydrochloric acid (2M, 50 mL), dried (phase separator) and concentrated in vacuo to give the title compound as a yellow oil (808 mg, 3.51 mmol). δH (methanol-d4, 400 MHz) 7.87 (1H d), 7.76 (1H dd), 7.11 (1H, d) 5.59-5.54 (1H, m), 2.68 (2H, q), 2.25-2.15 (4H, m), 1.84-1.67 (4H, m), 1.20 (3H, t). LCMS (ES): C15H18O2 requires 230; found 229 (M−H+).

Provenance & Evidence