Dimethylformamide → Terephthalic acid monomethylester chloride

Participants

Reaction Conditions

Reaction Steps

A suspension of 10.00 g (55.51 mmol) of monomethyl terephthalate in 90 mL of 1,2-dimethoxyethane was stirred, while it is cooled in a cold bath at 10° C. To the suspension were added 2.0 mL of N,N-dimethylformamide and 6.61 g (52.75 mmol) of thionyl chloride in this order, and the suspension was stirred at 60° C. to 65° C. for 1 hour. The mixture was cooled, and 6.83 g (52.82 mmol) of diisopropylethylamine was added dropwise to the mixture under cooling with ice bath. Subsequently, the reaction mixture was stirred at room temperature, and the stirring was stopped 30 minute after the internal temperature had reached 20° C. The reaction mixture was placed in a 200-mL flask to yield 109.49 g of [terephthalic acid monomethyl ester chloride/diisopropylethylamine] (the content of terephthalic acid monomethyl ester chloride: 8.89 g) as a slightly tannish solution.

Provenance & Evidence