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
Conditions
- Temperature
- 50 °C
Procedure
26 g of 1-benzyloxy-9,9,10,10,10-pentafluorodecane are dissolved in 1000 ml of abs. methylene chloride, treated at 0° C. with 28.9 ml of N,N-dimethylaniline and stirred for 5 minutes. 41.1 g of aluminium trichloride are then added in portions and the reaction mixture is warmed to 50° C. for 45 minutes. For work-up, the mixture is allowed to come to room temperature, stirred into 2N hydrochloric acid, extracted 3 times with methylene chloride, and the organic phase is washed with sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo. The crude product is chromato-graphed on silica gel using a hexane-ethyl acetate radient. 7.8 g of 9,9,10,10,10-pentafluorodecan-1-ol are obtained as an oil.
Workup
- customto come to room temperature
- extractionextracted 3 times with methylene chloride
- washthe organic phase is washed with sodium chloride solution
- dry with materialdried over magnesium sulphate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-1a8e179c2bdc46d2af0700cc52dad8c5
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06677324B1
Reaction notes
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