Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 19774074, compound

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Reaction Conditions

Reaction Steps

A mixture of 5 (7.23 g, 2.94 mmol) and pyridinium p-toluenesulfonate (0.74 g, 2.94 mmol) in acetone (150 mL) was stirred in a cold room at 4° C. for 5 days. The mixture was neutralized with sodium bicarbonate solution, and diluted with toluene. After evaporation of acetone, the residue was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, and dried over sodium sulfate. Filtration and concentration gave 9.22 g of an oily material, which was purified by column chromatography (silica gel 60 g, 4-16% ethyl acetate in n-hexane) to give 6.16 g (quantitative) of 6, as a pale yellow oil.

Provenance & Evidence