4-Isopropylbenzoic Acid → 4-(Propan-2-yl)cyclohexane-1-carboxylic acid

HRID 1194793Notes

Reaction equation

HRID 1194793 reaction equation
[OH:1][C:2]([C:4]1[CH:12]=[CH:11][C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][CH:5]=1)=[O:3].[H][H]>[Pt]=O.C(O)(=O)C>[CH:8]([CH:7]1[CH2:11][CH2:12][CH:4]([C:2]([OH:3])=[O:1])[CH2:5][CH2:6]1)([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 108204-Isopropylbenzoic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 815264-(Propan-2-yl)cyclohexane-1-carboxylic acidYield 96.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

Platinum oxide (500 mg) as a catalyst was suspended in acetic acid (50 ml) and cumic acid (10 g, 61 mmole) was added thereto. The mixture thus obtained was stirred vigorously for 2 hours at room temperature under a pressure of hydrogen 5 kg/cm2. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to a solid state. The resultant substance was distilled under reduced pressure of 1 mmHg (1.3×10-3 kg/cm2), at 113°-116° C. to obtain 4-isopropylcyclohexane carboxylic acid yielding 10 g (96%) ij a ratio of 3 parts of cis-form per 1 part of trans-form by weight.

Workup

  1. customThe mixture thus obtained
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure to a solid state
  4. distillationThe resultant substance was distilled under reduced pressure of 1 mmHg (1.3×10-3 kg/cm2), at 113°-116° C.

Sources & evidence

ORD record
ord-c19140469ac848ef9935800ae7a14f9a
Source dataset
uspto-grants-1989_03
Patent number
US04816484

Reaction notes

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