Acetic Acid → 1,3-Cyclohexanedicarboxylic acid

HRID 352253

Reaction equation

HRID 352253 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.C(O)(=O)C>CO.[Rh]>[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 176Acetic AcidHCID 8496Isophthalic Acid

Product 1

HCID 1072051,3-Cyclohexanedicarboxylic acidYield 96.3%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of isophthalic acid (500 g, 3 mol) in methanol (2.8) was added 5% Rhodium-on-alumina catalyst (50 g) and acetic acid (150 ml). The reaction mixture was shaken under hydrogen (50 psi) at room temperature overnight. The mixture was filtered through celite. To this solution was added fresh 5% Rhodium-on-alumina catalyst (25 g), and the mixture was shaken under 50 psi of hydrogen for another 24 hours. The final reaction mixture was filtered through celite. The solution was concentrated under vacuum to give 493 g of the title compound as a white powder (96.3% yield). m.p. 163-165° C.

Workup

  1. filtrationThe mixture was filtered through celite
  2. additionTo this solution was added fresh 5% Rhodium-on-alumina catalyst (25 g)
  3. stirringthe mixture was shaken under 50 psi of hydrogen for another 24 hours
  4. customThe final reaction mixture
  5. filtrationwas filtered through celite
  6. concentrationThe solution was concentrated under vacuum

Sources & evidence

ORD record
ord-b8586187541a44f9a7a1ae0185bd1704
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Linked notes

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