3-Phenyllactic acid, (S)- → (S)-a-Hydroxy-cyclohexanepropanoic acid

HRID 1532870Notes

Reaction equation

HRID 1532870 reaction equation
[C:1]1([CH2:7][C@H:8]([OH:12])[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Rh]>[CH:1]1([CH2:7][C@H:8]([OH:12])[C:9]([OH:11])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 4447183-Phenyllactic acid, (S)-

Product 1

HCID 12756210(S)-a-Hydroxy-cyclohexanepropanoic acid

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (S)-3-phenyllactic acid (20g) in ethanol (250mL) was added 5% rhodium on alumina (2.5 g), and the reaction was shaken under 4atm H2 for 24 h. The reaction was filtered, and concentrated to give product as a white solid (≈20 g). 1H NMR (300 MHz, CDCl3) δ0.86-1.07 (m, 2H), 1.08-1.39 (m, 3H), 1.54-1.91 (m, 9H), 4.33 (dd, J=9.3, 3.6 Hz, 1H). MS(CI/NH3) m/e: (M+NH4)+ 190.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4fabfc97bcc94e35b7c893d639392255
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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