HCID 2724160, compound → 4-(Propan-2-yl)cyclohexane-1-carboxylic acid

HRID 1194792Notes

Reaction equation

HRID 1194792 reaction equation
[CH3:1][C:2]([C@@H:4]1[CH2:9][CH:8]=[C:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1)=[CH2:3].[H][H]>[Pt]=O.C(O)(=O)C>[CH:2]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:1]

Participants

5

Reactant 2

HCID 2724160HCID 2724160, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 815264-(Propan-2-yl)cyclohexane-1-carboxylic acidYield 93%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

Platinum oxide (200 mg) as a catalyst was suspended in acetic acid (20 ml), and then (s)-(-)-perillic acid (2 g, 12 mmole) was added. The mixture thus obtained was stirred for 8 hours at room temperature under a current of hydrogen gas. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to a dryness. The matter was recrystallized from methanol-water to obtain 4-isopropyl cyclohexane carboxylic acid (1.9 g, yield 93%).

Workup

  1. customThe mixture thus obtained
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure to a dryness
  4. customThe matter was recrystallized from methanol-water

Sources & evidence

ORD record
ord-e7171b2f653a41ab97c03b81523dc244
Source dataset
uspto-grants-1989_03
Patent number
US04816484

Reaction notes

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