Thionyl Chloride → 2-(p-Toluenesulfonyl)ethyl 5-chlorosulfonyl-2-methoxybenzoate

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A mixture of 5-chlorosulfonyl-2-methoxybenzoic acid (Intermediate 6, 3.0 g, 12.0 mmol) and SOCl2 (6 mL) was heated to reflux temperature for 2 h. Then excess SOCl2 was removed by distillation. The resulting residual oil was dissolved in 20 mL of CH2Cl2 and 2-(p-toluenesulfonyl)ethanol (available from Aldrich 2.0 g, 10 mmol) in 10 mL of CH2Cl2 was added at room temperature. The resulting mixture was heated to reflux temperature for 3 h. Thereafter volatile materials were removed under reduced pressure and the residual oil was purified by column chromatography (silica gel, hexane:CH2C2=1:1 to CH2Cl2) to give 3.5 g (81%) of 2-(p-toluenesulfonyl)ethyl 5-chlorosulfonyl-2-methoxybenzoate (Intermediate 7) as clear thick oil.

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