Hydrochloric Acid → trans-3-(2,2-Difluoroethenyl)-2,2-dimethylcyclopropanecarboxylic acid

A stirred solution of 10.0 g (0.049 mole) of ethyl trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarboxylate and 30 ml of a 10% aqueous sodium hydroxide solution in 60 ml of ethanol was heated at reflux for 1.25 hours, then stirred at room temperature for approximately 18 hours. The reaction mixture was heated at 70° C. for an additional 1.5 hours, then cooled to room temperature and poured into 150 ml of a 5% aqueous hydrochloric acid solution. The resultant mixture was extracted with three 50 ml portions of diethyl ether. The extracts were combined, washed twice with water (50 ml) and once with a saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate. The organic solution was filtered, and the filtrate evaporated under reduced pressure to yield 7.95 g of trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarboxylic acid as an oil.

1. temperatureat reflux for 1.25 hours
2. temperatureThe reaction mixture was heated at 70° C. for an additional 1.5 hours
3. temperaturecooled to room temperature
4. extractionThe resultant mixture was extracted with three 50 ml portions of diethyl ether
5. washwashed twice with water (50 ml) and once with a saturated aqueous sodium chloride solution
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationThe organic solution was filtered
8. customthe filtrate evaporated under reduced pressure

ORD record

ord-580e5de538c94198bea65c0e63702264

Source dataset

uspto-grants-1985_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04552892