Catechol → 2-(1-Chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole

Temperature

75 °C

110 g of pyrocatechol were dissolved in 1500 ml of acetonitrile, and 200 g of triethylamine were added. 235 g of 2,3-dichloro-1,1,1,4,4,4-hexafluoro-2-butene were added dropwise to the mixture at 75° C. The mixture was subsequently stirred at 75° C. for 2 hours. 1200 ml of the solvent were then distilled off in vacuo and the residue was taken up in 1500 ml of water. The product was extracted with diethyl ether and the organic phase was washed twice with 10% strength by weight aqueous sodium hydroxide solution and once with water. After drying with magnesium sulphate, the organic phase was concentrated and the residue was subjected to fractional distillation in vacuo. The yield was 258 g (=84% of theory). The boiling point was 63° C. under 12 mbar. The NMR spectra showed the following characteristic absorptions: 19F-NMR: -66.8 and -79.7 ppm. 1H-NMR: 4.71 ppm.

1. distillation1200 ml of the solvent were then distilled off in vacuo
2. extractionThe product was extracted with diethyl ether
3. washthe organic phase was washed twice with 10% strength by weight aqueous sodium hydroxide solution and once with water
4. dry with materialAfter drying with magnesium sulphate
5. concentrationthe organic phase was concentrated
6. distillationthe residue was subjected to fractional distillation in vacuo

ORD record

ord-bc3f0eeb02a14ddcb37aa204543fe679

Source dataset

uspto-grants-1996_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05482956