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

HRID 2240309Notes

Reaction equation

HRID 2240309 reaction equation
[C:1]1([C@:7]([OH:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>CO.[Pd]>[CH:11]1([C@@:7]([OH:17])([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]([OH:10])=[O:9])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 10585664(S)-Cyclohex-1-enyl-hydroxy-phenyl-acetic acid

Product 1

HCID 777377Cyclohexylphenylglycolic acid, (-)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-cyclohex-1-enyl-hydroxy-phenyl-acetic acid (120 g, 0.517 mol) is dissolved in methanol (678 ml) under an inert atmosphere of Argon and then treated with palladium on carbon (6 g, 10% w/w). The resulting suspension is stirred under an atmosphere of hydrogen for 22 hours and then filtered through celite. The solvent is removed in vacuo to yield the titled product.

Workup

  1. filtrationfiltered through celite
  2. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-74ed25c5b64b47cd88f5ecc5f67e083d
Source dataset
uspto-grants-2010_05
Patent number
US07723356B2

Reaction notes

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