Sodium Hydroxide → 4-[Cyclopropyl(hydroxy)methyl]benzoic acid

Participants

Reaction Conditions

Reaction Steps

To ethyl 4-(cyclopropanecarbonyl)benzoate (400 mg, 1.83 mmol) in ethanol (10 mL) was added at room temperature NaBH4 (69 mg, 1.83 mmol) and the reaction mixture was stirred for 1 hour. The reaction mixture was then concentrated in vacuo and NaOH (1.5 g, 9.38 mmol) and dioxane (1.5 mL) were added and the reaction mixture was heated at 80° C. for 3 hours. The reaction mixture was concentrated in vacuo to half the volume and pH was adjusted to 2 with 3 N HCl. The aqueous layer was extracted with ethyl acetate (3×10 mL), and the combined organics were washed with brine solution (5 mL), dried over MgSO4 and concentrated in vacuo to give 4-[cyclopropyl(hydroxy)methyl]benzoic acid (300 mg, 85%). ESI-MS m/z calc. 192.2. found 193.5 (M+1)+; Retention time: 0.78 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 7.89 (d, J=8.1 Hz, 2H), 7.49 (d, J=8.1 Hz, 2H), 5.33 (d, J=4.4 Hz, 1H), 4.04 (dd, J=7.3, 4.3 Hz, 1H), 1.12-0.87 (m, 1H), 0.54-0.20 (m, 4H).

Provenance & Evidence