Benzyl 4,4-difluoro-1-hydroxycyclohexanecarboxylate → 4,4-Difluoro-1-hydroxycyclohexane-1-carboxylic acid

HRID 1160617Notes

Reaction equation

HRID 1160617 reaction equation
[F:1][C:2]1([F:19])[CH2:7][CH2:6][C:5]([OH:18])([C:8]([O:10]CC2C=CC=CC=2)=[O:9])[CH2:4][CH2:3]1.[H][H]>CCOC(C)=O.[Pd]>[F:1][C:2]1([F:19])[CH2:3][CH2:4][C:5]([OH:18])([C:8]([OH:10])=[O:9])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 68715338Benzyl 4,4-difluoro-1-hydroxycyclohexanecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 401519704,4-Difluoro-1-hydroxycyclohexane-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl 4,4-difluoro-1-hydroxycyclohexanecarboxylate (2.76 g, 10.21 mmol) was dissolved in 68 mL of EtOAc and a suspension of 10% Palladium on Carbon (1.1 g in 5 mL of EtOAc) was added. The mixture was stirred at room temperature under at atmosphere of hydrogen for 45 minutes (balloon), and the reaction mixture was filtered through a glass micropore filter and concentrated under vacuum to provide 4,4-difluoro-1-hydroxy-cyclohexanecarboxylic acid.

Workup

  1. additionwas added
  2. filtrationthe reaction mixture was filtered through a glass micropore
  3. filtrationfilter
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-948c8e05fe7c49c8a15db182f8565471
Source dataset
uspto-grants-2010_10
Patent number
US07816380B2

Reaction notes

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