2-Hydroxy-p-toluic acid → Methyl 2-methoxy-4-methylbenzoate

Participants

Reaction Steps

To a mixture of 2-hydroxy-4-methylbenzoic acid (30.43 g, 200 mmol), K2CO3 (62.19 g, 450 mmol) and DMF (600 mL) was added methyl iodide (28.01 mL, 450 mmol). The reaction was stirred for 18 h, poured into ice/water (1.2 L), and extracted with EtOAc (2×300 mL). The combined organic layer was washed with brine, satd NaHCO3 and dried (MgSO4). The resulting solution was concentrated and distilled to give the title compound as a pale yellow liquid (32.73 g, 91%, bp 120-4° C./1333 Pa, 10 mm).

Provenance & Evidence