Chlorotrimethylsilane → Methyl 5-methylsalicylate

Participants

Reaction Steps

To a solution of 5-methylsalicylic acid (7.24 g) in methanol (250 ml) was added trimethylsilyl chloride (60 ml). The mixture was heated at reflux for 2 hours and stirred at room temperature overnight. A further 60 ml trimethylsilyl chloride was added and the mixture heated at reflux for 6 hours. The mixture was evaporated and the residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was dried (MgSO4) and evaporated to give the crude product. Yield 5.87 g. Used directly in the next step.

Provenance & Evidence