Methyl iodide → Methyl 3-hydroxy-5-methoxybenzoate

Participants

Reaction Steps

Methyl iodide (36 ml) was added to a mixture of methyl 3,5-dihydroxybenzoate (104 g), potassium carbonate (79 g) and dimethylformamide (1200 ml) and the mixture was stirred at ambient temperature for 16 hours. The mixture was partitioned between water (2.5 litre) and petrol (b.p. 60°-80° C., 600 ml). The aqueous layer was washed with petrol (b.p. 60°-80° C., 600 ml) and then extracted with toluene (2×1 litre). The toluene extracts were combined, washed with water (4×800 ml), dried (MgSO4) and evaporated to give methyl 3-hydroxy-5-methoxybenzoate as an oil (33 g, 30%).

Provenance & Evidence