(2R)-2-methyl-3-phenylpropanoic acid → (2R)-3-cyclohexyl-2-methylpropanoic acid

HRID 1379591

Reaction equation

HRID 1379591 reaction equation
[CH3:1][C@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4]>CO.[Rh]>[CH3:1][C@H:2]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 1

HCID 5287791(2R)-2-methyl-3-phenylpropanoic acid

Product 1

HCID 22877219(2R)-3-cyclohexyl-2-methylpropanoic acidYield 78.3%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of α(R)-methylbenzenepropionic acid (3.0 g, 18 mmol) and 5% rhodium on alumina (800 mg) in methanol (100 mL) was shaken under 40 p.s.i. of H2 on a Parr hydrogenation apparatus. After 15 h, the mixture was filtered through diatomaceous earth and concentrated to afford α(R)-methylcyclohexanepropionic acid as a clear liquid (2.4 g, 77%). 1H NMR (CDCl3) δ 2.62-2.53 (m, 1H), 1.79-1.59 (m, 6H), 1.38-1.16 (m, 5H), 1.17 (d, J=7 Hz, 3H), 0.95-0.83 (m, 2H).

Workup

  1. filtrationthe mixture was filtered through diatomaceous earth
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4d6b0cf46368473e8809b57ba6515045
Source dataset
uspto-grants-1997_09
Patent number
US05672586

Linked notes

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