Catechol → 2-(1-Chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole
Reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].C(N(CC)CC)C.Cl[C:17](=[C:22]([Cl:27])[C:23]([F:26])([F:25])[F:24])[C:18]([F:21])([F:20])[F:19]>C(#N)C>[Cl:27][CH:22]([C:17]1([C:18]([F:19])([F:20])[F:21])[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2]1)[C:23]([F:26])([F:25])[F:24]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
110 g of pyrocatechol were dissolved in 1,500 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 at 75° C. to the mixture. Stirring was continued for 2 hours at 75° C. 1,200 ml of the solvent were then distilled off in vacuo and the residue was taken up in 1,500 ml of water. The product was extracted with diethyl ether and the organic phase was washed 2 times with 10% strength by weight aqueous sodium hydroxide solution and 1 time with water. After drying with magnesium sulphate the product was concentrated and subjected to fractional distillation in vacuo. The yield was 258 g (=84% of theory). The boiling point was 63° C. at 12 mbar. The NMR spectra showed the following characteristic absorptions: 19F-NMR: -66.8 and -79.7 ppm; 1H-NMR: 4.71 ppm.
Workup
- distillation1,200 ml of the solvent were then distilled off in vacuo
- extractionThe product was extracted with diethyl ether
- washthe organic phase was washed 2 times with 10% strength by weight aqueous sodium hydroxide solution and 1 time with water
- dry with materialAfter drying with magnesium sulphate the product
- concentrationwas concentrated
- distillationsubjected to fractional distillation in vacuo
Sources & evidence
- ORD record
- ord-8e56d68631424de685e4408ec8fe9f2b
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05585395
Reaction notes
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