Hydrochloric Acid → 4-(Cyanomethyl)-3-methoxybenzoic acid

Participants

Reaction Steps

A solution of methyl 4-(cyanomethyl)-3-ethoxybenzoate (18 g, 88 mmol) in 150 mL of MeOH:THF:H2O (3:3:1) was treated with lithium hydroxide monohydrate (11 g, 263 mmol) at 22° C. for overnight. Then 10% aqueous HCl (100 mL) was added to quench the reaction, the mixture was extracted with EtOAc (3×200 mL), the combined organic extracts were washed with brine (100 mL) and dried (MgSO4), filtered and concentrated in vacuo to afford 4-(cyanomethyl)-3-methoxybenzoic acid as a white solid. MS (ESI) 192 (M+H)+.

Provenance & Evidence