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

A stirred solution of ethyl trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarboxylate (10.0 g; 0.049 mole) and 30 ml of an aqueous 10% 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 an aqueous 5% 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 an aqueous saturated 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 an aqueous saturated 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-138d2ffdcd814db5aeffa18d19ff0450

Source dataset

uspto-grants-1985_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04507317