Hydrochloric Acid → 9,9,10,10,10-Pentafluorodecan-1-ol
Reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])C1C=CC=CC=1.CN(C)C1C=CC=CC=1.[Cl-].[Cl-].[Cl-].[Al+3].Cl>C(Cl)Cl>[F:22][C:17]([F:23])([C:18]([F:19])([F:20])[F:21])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8]Participants
6
Procedure
26 g of 1-benzyloxy-9,9,10,10,10-pentafluoro-decane is dissolved in 1000 ml of absolute methylene chloride, mixed with 28.9 ml of N,N-dimethylaniline at 0° C. and stirred for 5 minutes. Then, 41.1 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, the organic phase is washed with common salt solution, 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. 7.8 g of 9,9,10,10,10-pentafluoro-decan-1-ol is obtained as an oil.
Workup
- temperaturethe reaction mixture is heated for 45 minutes to 50° C
- customto come to room temperature
- extractionextracted 3 times with methylene chloride
- washthe organic phase is washed with common salt solution
- customdried on magnesium sulfate
- concentrationconcentrated by evaporation in a vacuum
- customThe crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient
Sources & evidence
- ORD record
- ord-7aec45e5edc446fd9160f696f21fd1f4
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06780855B2
Reaction notes
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