Hydrochloric Acid → 3,3-Difluoro-2-trifluoromethyl-2,3,3a,4,5,6,7,7a-octahydrobenzofuran-2,3a-diol

Participants

Reaction Conditions

Reaction Steps

In a nitrogen atmosphere at −5° C., 1000 ml of 2.6M n-butyllithium in hexane was added to a mixture of 224 g of 1,1,1,3,3,3-hexafluoro-2-propanol and 1000 g of tetrahydrofuran, followed by one hour of stirring at 5° C. Then 164 g of 2-chlorocyclohexanone was added at 5° C. The mixture was stirred for 10 hours, after which dilute hydrochloric acid was added to quench the reaction and neutralize the reaction mixture. Then 1200 g of a 10% aqueous solution of sodium hydroxide was added to the reaction mixture, from which an aqueous layer was separated. It was made acidic by adding 560 g of 20% dilute hydrochloric acid and combined with 1000 g of toluene, after which an organic layer was separated. The organic layer thus separated was concentrated and purified by recrystallization from hexane, obtaining 201 g of the product (yield 63%).

Provenance & Evidence