1,1,1,3,3,3-Hexafluoro-2-propanol → Hexafluoroisopropyl beta-chloroisobutyrylcarbamate

Participants

Reaction Steps

To a solution of beta-chloroisobutyryl isocyanate (7.38 g; 50 mmol) in chloroform (50 ml), a solution of 1,1,1,3,3,3-hexafluoroisopropanol (8.4 g; 50 mmol) in chloroform (10 ml) was dropwise added at 10° C. under ice-cooling. After completion of the addition, the resultant mixture was stirred for 1 hour, whereby hexafluoroisopropyl beta-chloroisobutyrylcarbamate was produced. A solution of triethylamine (5.05 g; 50 mmol) in chloroform (50 ml) was added to the reaction mixture in 30 minutes under ice-cooling. The reaction mixture was stirred for 1 hour, and precipitated triethylamine hydrochloride (6.87 g) was eliminated by filtration. The filtrate was concentrated under reduced pressure to give hexafluoroisopropyl N-methacryloylcarbamate (13.4 g), which was recrystallized from benzene to give colorless prisms. M.P., 112.5°-113° C.

Provenance & Evidence