Water → Methyl 3-tert-butyl-4-methoxybenzoate

Participants

Reaction Steps

Preparation C11, Step 1: 3-tert-butyl-4-hydroxybenzoic acid (1.00 g, 5.15 mmol, 1 eq), dimethyl sulfate (1.07 mL, 11.3 mmol, 2.2 eq) and potassium carbonate (2.85 g, 20.6 mmol, 4 eq) were refluxed in methyl ethyl ketone (20 mL) for 3 hours. Worked up by adding H2O (20 mL) then stripped off the methyl ethyl ketone. The aqueous was extracted 3 times with diethyl ether (25 mL). The organic layers were combined, dried (sodium sulfate) and stripped to give methyl 3-tert-butyl-4-methoxybenzoate (1.12 g) of an amber oil Yield=97%. LCMS detects (M+H)+=223.23.

Provenance & Evidence