Hydrochloric Acid → 8,8,9,9,9-Pentafluorononan-1-ol

Participants

Reaction Steps

16 g of 1-benzyloxy-8,8,9,9,9-pentafluoro-nonane is dissolved in 700 ml of absolute methylene chloride, mixed with 18.4 ml of N,N-dimethylaniline at 0° C. and stirred for 5 minutes. Then, 26.4 g of aluminum trichloride is added in portions, and the reaction mixture is heated for 45 minutes to 50° C. For working-up, the batch is allowed to come to room temperature, it is stirred into 2N hydrochloric acid, extracted 3 times with methylene chloride, dried on magnesium sulfate and concentrated by evaporation in a vacuum. The crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient. 8.6 g of 8,8,9,9,9-pentafluoro-nonan-1-ol is obtained as an oil.

Provenance & Evidence