Methanol → Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

Participants

Reaction Conditions

Reaction Steps

A 50 ml round-bottom flask equipped with a stir bar under a dry nitrogen atmosphere was charged with 4-methylsalicylic acid (1.5 g, 10.0 mmoles, 1.0 eq) followed by dry MeOH (15 ml). The reaction mixture was cooled to 0° C. on an ice bath and neat SOCl2 (1.1 ml, 15.0 mmoles, 1.5 eq) was added dropwise. The reaction was allowed to warm to room temperature and then stirred at reflux for 5 hrs. After that time, excess MeOH was removed in vacuo, the residue dissolved in EtOAc and extracted with saturated NaHCO3, the organic layer was dried with MgSO4 and filtered. Removal of excess solvent from the filtrate in vacuo provided 1.20 g (72%) of the title compound as a clear oil. (1H CDCl3, 400 MHz): δ 10.71 (s, 1H), 7.70 (d, J=8.1 Hz, 1H), 6.75 (s, 1H), 6.69 (d, J=8.1 Hz, 1H), 3.93 (s, 3H), 2.34 (s, 3H).

Provenance & Evidence