Sulfuric Acid → HCID 19788873, compound

HRID 1656844Notes

Reaction equation

HRID 1656844 reaction equation
FC(F)(F)C(F)=C(F)F.[F:10][C:11]([F:28])([F:27])[CH:12]([C:17](F)([F:25])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])[C:13]([F:16])([F:15])[F:14].S(=O)(=O)(O)[OH:30]>O>[F:10][C:11]([F:28])([F:27])[C:12]([OH:30])([CH:17]([F:25])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])[C:13]([F:16])([F:15])[F:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8302HexafluoropropyleneHCID 109141792H-Perfluoro(2-methylpentane)

Product 1

HCID 19788873HCID 19788873, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To prepare 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol, commercially available hexafluoropropene may be oligomerized with commercially available trimethylamine in a dipolar aprotic solvent such as commercially available tetrahydrofuran to provide (CF3)2C:CFCF2CF3 which is then reacted with commercially available hydrogen fluoride to yield 2-trifluoromethyl-1,1,1,3,3,4,4,5,5,5-decafluoropentane as taught by W. Brunskill et al., "Anionic Oligomerisation of Hexafluoropropene: Fission of a Carbon-Carbon Bond by Fluoride Ion", Chemical Communications, 1444 (1970). The 2-trifluoromethyl-1,1,1,3,3,4,4,5,5,5-decafluoropentane may then be dehydrohalogenated and then reacted with sulfuric acid and then water to form 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol.

Sources & evidence

ORD record
ord-e9f51891d4d3470c90928f867920a72d
Source dataset
uspto-grants-1993_10
Patent number
US05254755

Reaction notes

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