Isophthalic Acid → 1,3-Cyclohexanedicarboxylic acid

HRID 352255

Reaction equation

HRID 352255 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=1.[H][H]>C(O)(=O)C.[Pt]=O>[CH:2]1([C:1]([OH:12])=[O:11])[CH2:10][CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3]1

Participants

5

Reactant 2

HCID 8496Isophthalic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 1072051,3-Cyclohexanedicarboxylic acidYield 95%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent2×

Procedure

To a suspension of isophthalic acid (5.0 g, 30.1 mmol) in 45 ml of acetic acid was added a slurry of 0.1 g of platinum oxide in 5 ml of acetic acid. The resulting mixture was stirred under 50 psi of hydrogen at 25° C. for 16 hours. NMR analysis (DMSO-d6) at this time showed complete reduction of starting material. The reaction mixture was filtered through Celite and the filter cake was rinsed with methanol. The combined filtrate and washes were concentrated under reduced pressure, using heptane to azeotropically remove residual acetic acid. Trituration of the resultant semi-solid with heptane and filtration of the precipitate provided 4.92 g (95%) of the title compound as a white powder. mp: 163-165° C.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe filter cake was rinsed with methanol
  3. concentrationThe combined filtrate and washes were concentrated under reduced pressure
  4. filtrationTrituration of the resultant semi-solid with heptane and filtration of the precipitate

Sources & evidence

ORD record
ord-1ef743e214814c4e9dab665f9bf6af95
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Linked notes

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