(S)-Cyclohex-1-enyl-hydroxy-phenyl-acetic acid → Cyclohexylphenylglycolic acid, (+)-

HRID 843281

Reaction equation

HRID 843281 reaction equation
[C:1]1([C@@:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([OH:11])[C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[H][H]>CO.[Pd]>[CH2:15]1[CH2:14][CH2:13][CH:12]([C@@:7]([OH:11])([C:8]([OH:10])=[O:9])[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 10585664(S)-Cyclohex-1-enyl-hydroxy-phenyl-acetic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 777375Cyclohexylphenylglycolic acid, (+)-Yield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-Cyclohexenyl phenyl glycolic acid (1.11 g, 4.78 mmol) in methanol (16 mL) was added 10% Pd/C (0.11 g). The reaction was subjected to 1 ATM of Hydrogen and was allowed to stir for 18 h. the reaction mixture was filtered through a plug of celite and concentrated in vacuo to provide 1.01 g of (S)-CHPGA (91%, 98.3% e.e.).

Workup

  1. filtrationwas filtered through a plug of celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eda513b977ac4ffe8c2d34e66594a125
Source dataset
uspto-grants-2002_04
Patent number
US06376684B1

Linked notes

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