Pyridine → 1,1-Dimethylethyl 4-methylbenzoate

Participants

Reaction Steps

8.55 ml (64.69 mmol) of 4-toluoyl chloride are added dropwise to 10.52 ml (109.96 mmol) of tert-butanol and 10.46 ml (129.37 mmol) of pyridine while cooling in ice. The mixture is stirred at room temperature for 12 hours. After reaction is complete, water is added and the mixture is extracted with ethyl acetate. The organic phase is washed successively with sodium bicarbonate solution, water and sodium chloride solution, dried over sodium sulphate and evaporated. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 50:1). 7.76 g (40.36 mmol, 62% yield) of the title compound are obtained as a colourless oil.

Provenance & Evidence