Water → HCID 19969101, compound

HRID 974715

Reaction equation

HRID 974715 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9](F)[C:8]([F:13])=[C:7]([F:14])[C:3]=1[C:4]([OH:6])=[O:5].[F:15][C:16]([F:28])([C:19]([F:27])([F:26])[C:20]([F:25])([F:24])[CH:21]([F:23])[F:22])[CH2:17][OH:18].[H-].[Na+].O>CN(C)C=O.C(OCC)(=O)C>[F:15][C:16]([F:28])([C:19]([F:26])([F:27])[C:20]([F:24])([F:25])[CH:21]([F:22])[F:23])[CH2:17][O:18][C:9]1[C:8]([F:13])=[C:7]([F:14])[C:3]([C:4]([OH:6])=[O:5])=[C:2]([F:1])[C:10]=1[F:11]

Participants

7

Reactant 4

HCID 962WaterHCID 96412,2,3,3,4,4,5,5-Octafluoro-1-pentanolHCID 11770Pentafluorobenzoic acidHCID 24758Sodium hydride

Product 1

HCID 19969101HCID 19969101, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2,3,4,5,6-pentafluorobenzoic acid (1 g) and 2,2,3,3,4,4,5,5-octafluoropentanol (1.18 g) in N,N-dimethylformamide (5 ml) was added 62% sodium hydride (0.39 g) at room temperature. The mixture was stirred at the same temperature for 1 hour, and thereto was added a mixture of water and ethyl acetate. The separated organic layer was washed with water and brine, dried over magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by chromatography on silica gel to give 4-(2,2,3,3,4,4,5,5-octafluoropentyloxy)-2,3,5,6-tetrafluorobenzoic acid (923.0 mg).

Workup

  1. additionwas added
  2. washThe separated organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-0017f2390d414d74bd6068e2c0f7ef96
Source dataset
uspto-grants-1997_03
Patent number
USH0001638

Linked notes

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