Dimethylformamide → Methyl 4-hydroxy-3-methylbenzoate

To a solution of 4-hydroxy-3-methylbenzoic acid (10.0 g, 65.7 mmol) and DMF (100 μL) in methanol (35 mL) was added dropwise thionyl chloride (7.8 g, 4.8 mL, 65.7 mmol). The reaction mixture was allowed to stir at room temperature for 2 hours. The reaction mixture was quenched with the addition of aqueous saturated sodium bicarbonate solution (50 mL) and methanol was removed in vacuo. The aqueous layer was then extracted with EtOAc (3×50 mL). The organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to provide methyl 4-hydroxy-3-methyl-benzoate (10.5 g, 96%) as a light brown solid. ESI-MS m/z calc. 166.4. Found 167.4 (M+1)+; Retention time: 1.09 minutes (3 min run).