Methanol → HCID 21910052, compound

Participants

Reaction Steps

A 5-L round bottom 3-neck flask equipped with a −78° C. condenser and mechanical stirred was charged with 1025 g of methanol and 300 g of sodium fluoride. 3-Trifluoromethoxytetrafluoropropionyl fluoride (1561 g, 6.7 mol), prepared as described in Example 1 of U.S. Pat. No. 6,482,979 (Hintzer et al.), was added to the flask at −20° C. The reaction mixture was washed with 800 g water and phased split to give 1490 g of methyl-3-trifluoromethoxypropionate for a 91% yield after fractionation. A 5-liter round bottom flask equipped with a mechanical stirrer, a −78° C. condenser and addition funnel was charged with 1463 g of methyl-3-trifluoromethoxypropionate (6 mol) and 940 g of dimethylformamide. The mixture was stirred at room temperature and 125 g of ammonia (7.4 mol) was added to convert the ester to amide. Methanol was vacuum stripped and 1160 g of pyridine (14.7 mol) was added. The mixture was cooled to −14° C. and 1493 g of trifluoroacetic anhydride (7.1 mol) was added. After addition was completed, 1 kg of water was added and the product began to reflux on the condenser. A total of 1165 g of heptafluoro-3-methoxypropanenitrile, CF3OCF2CF2CN was obtained after distillation.

Provenance & Evidence