Dimethyl Sulfate → Methyl p-toluenesulfonate

Participants

Reaction Steps

To a suspension of p-toluenesulfonic acid dihydrate (10 g, 0.05 mol) in methylene chloride (50 mL), diphenylamine (10.8 g, 0.06 mol) was added dropwise, and the mixture was reacted at room temperature for 1 hour. After completion of the reaction, the solvent was evaporated to dryness under the reduced pressure to obtain a crude product containing diphenylammonium p-toluenesulfonate salt. To a suspension of this crude product (5 g, 0.011 mol) in cyclohexane (50 mL), dimethyl sulfate (3.0 g, 0.023 mol) was added, and the mixture was reacted at 80° C. for 2 hours. The reaction liquid was condensed under the reduced pressure to obtain the desired product of methyl p-toluenesulfonate. Quantitative analysis by 1H-NMR showed a conversion rate of 63%.

Provenance & Evidence