4-Toluenesulfonyl chloride → 2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

Participants

Reaction Conditions

Reaction Steps

A 300 gallon glass lined reactor was charged with p-toluene sulfonyl chloride (2) and methylene chloride. A second 300 gallon glass lined reactor was charged with USP water, sodium hydroxide, methylene chloride, triethyleneglycol monomethyl ether (TEG) (1), and benzyltriethyl ammonium chloride. The p-toluene sulfonyl chloride solution was slowly added over 2 hours to the TEG solution while maintaining a temperature of 0-25° C. The reaction mixture was agitated for 1 hour and sampled for reaction completion analysis by HPLC. The product was isolated by separating the methylene chloride layer (product layer) from the aqueous layer. The organic layer was washed twice with water and the methylene chloride was replaced with toluene by vacuum distillation to yield 2-(2-(2-methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (Ts-TEG) (3).

Provenance & Evidence