Methanol → HCID 23236268, compound

Participants

Reaction Steps

A solution of 50 g (0.28 mol) of perfluoromethacryloyl fluoride in 100 ml of ether was stirred at 0°C while 9.0 g (0.28 mol) of methanol was added at a rate sufficient to keep the reaction mixture near 20°C. When the addition was complete, 100 g of anhydrous NaF was added, and the mixture was stirred while 5.4 g (0.30 mol) of water was added. The temperature was not allowed to go above 35°C. After having stood overnight, the reaction mixture was filtered and distilled. It was necessary to keep the pot temperature below 70°C to avoid excessive etching. 3,3-Difluoro-3-methoxy-2-trifluoromethylpropionic acid was obtained as 22.1 g (38%) of distillate, bp 45°C (0.5 mm); ir (neat): 3.25 (broad, OH), 5.72 (C=O), 7.5-9 μ (CF, COC); nmr (CCl4): 1H at 11.8 (singlet, 1, OH), 3.83 (sextet (quartet, JHF = 7.5 Hz, into triplets, JHF = 7.5 Hz), 1, CH), and 3.67 ppm (singlet, 3, OCH3); 19F at -65.1 ppm (triplet, JFF = 10.5 Hz, into doublets, JHF = 7.5 Hz, 3, CF3) and 14 lines from overlapping center lines of an AB pattern at -4233 Hz and -4247 Hz (both quartets, JFF = 10.5 Hz, into doublets, JHF = 7.5 Hz, 2, CF2).

Provenance & Evidence