3-Methylbenzoic acid → 3-Methylcyclohexanecarboxylic acid

HRID 1533884Notes

Reaction equation

HRID 1533884 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:9])=[O:8])[CH:2]=1>C(O)(=O)C.[Pt]=O>[CH3:10][CH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([OH:9])=[O:8])[CH2:2]1

Participants

4

Reactant 1

HCID 74183-Methylbenzoic acid

Product 1

HCID 1144903-Methylcyclohexanecarboxylic acidYield 84.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of m-toluic acid (13.6 g, 0.1 mole) in acetic acid was added platinum oxide (0.1 g) under nitrogen. The mixture was hydrogenated in a Parr shaker at 35 psi. Upon completion, the catalyst was removed by filtration and the filtrate was concentrated to dryness to give 12 g of the title compound. The NMR spectrum showed absorption at 0.84 (d, 3H), 0.90 (d, 3H), 0.99-1.13 (m, 1H), 2.21-1.46 (m, 3H), 1.54-1.65 (m, 3H), 1.70-1.98 (m, 2H) and 1.23-2.41 (m, 1H).

Workup

  1. customUpon completion, the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-a61c0a2aa0cc40e187d4fe48baeebf42
Source dataset
uspto-grants-1992_02
Patent number
US05086062

Reaction notes

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