Terephthaloyl chloride → Monomethyl terephthalate

Participants

Reaction Steps

A solution of 20.3 g (100 mmol) terephthaloyl chloride in 100 ml dichloromethane was added to 100 ml anhydrous methanol at 0° C. The reaction was left 1.5 h at rt. The reaction mixture was evaporated and the residue was dissolved dichloromethane. The organic phase was washed with saturated NaHCO3 aq. The organic phase was dried and evaporated. Yield 18.3 g (94.2 mmol, 94%). A solution of 18.3 g (94.2 mmol) of terephthalic acid dimethyl ester and 3.96 g (94.2 mmol) LiOH.H2O in anhydrous methanol (did not dissolve completely) was stirred for 5 d at rt. The solvent was evaporated and the product was dissolved in water. The aqueous phase was washed with dichloromethane. The aqueous phase was made acidic with 2 M HCl aq. The product precipitated from the aqueous phase. The product was filtered off and dried in vacuo. The product was dissolved in 1 L dry ethanol, and thereafter 4 l water was added slowly while stirring. The product precipitated slowly overnight at +4°C. The product was filtered and dried in vacuo. Yield 8.61 g (48 mmol, 51%)

Provenance & Evidence