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

HRID 1838895Notes

Reaction equation

C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])C1C=CC=CC=1.CN(C)C1C=CC=CC=1.[Cl-].[Cl-].[Cl-].[Al+3].Cl>C(Cl)Cl>[F:21][C:16]([F:22])([C:17]([F:18])([F:19])[F:20])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8]

Participants

Conditions

Temperature: 50 °C

Procedure

16 g of 1-benzyloxy-8,8,9,9,9-pentafluorononane are dissolved in 700 ml of abs. methylene chloride, treated at 0° C. with 18.4 ml of N,N-dimethylaniline and stirred for 5 minutes. 26.4 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, dried over magnesium sulphate and concentrated in vacuo. The crude product is chromato-graphed on silica gel using a hexane-ethyl acetate gradient. 8.6 g of 8,8,9,9,9-pentafluorononan-1-ol are obtained as an oil.

Workup

customto come to room temperature
extractionextracted 3 times with methylene chloride
dry with materialdried over magnesium sulphate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-bbef60aeff98475bb645cc9a49a0cc2f
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677324B1

Reaction notes

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