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

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Reaction Steps

A mixture of methyl 2,5-dihydroxybenzoate (2.5 g, 14.87 mmol), potassium carbonate (25 g, 181 mmol), and dry acetone (150 ml) was stirred at room temperature for 30 min. 4-Methylbenzenesulfonyl chloride (2.86 g, 15.00 mmol) was added portionwise and the mixture was refluxed for 7 h. (Bromomethyl)benzene (6.35 g, 37.2 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 petroleum ether:ethyl acetate=4:1 to yield the title compound as a white solid. 2.6 g.

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