4-Toluenesulfonyl chloride → Methyl 5-{[(4-methylphenyl)sulfonyl]oxy}-2-[(phenylmethyl)oxy]benzoate

Participants

Reaction Steps

A mixture of methyl 2,5-dihydroxybenzoate (10 g, 59.5 mmol), potassium carbonate (50.0 g, 362 mmol), and dry acetone (450 ml) was stirred at room temperature for 30 min. 4-Methylbenzenesulfonyl chloride (11.44 g, 60.0 mmol) was added portionwise and the mixture was refluxed for 7 h. (Bromomethyl)benzene (25.4 g, 149 mmol) was added and the resulting mixture was refluxed overnight. After cooling, the precipitate was filtered, and the filtrate was evaporated. The residue was loaded onto a silica gel column and was eluted with hexane/ethyl acetate=4:1 to yield the title compound as a yellow solid. 22 g.

Provenance & Evidence