2,4-Di-tert-butylphenol → Cyclohexanone, 2,4-bis(1,1-dimethylethyl)-

HRID 277316

Reaction equation

HRID 277316 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Rh]>[C:1]([CH:5]1[CH2:10][CH:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:8][CH2:7][C:6]1=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 73112,4-Di-tert-butylphenol

Product 1

HCID 114442Cyclohexanone, 2,4-bis(1,1-dimethylethyl)-Yield 91%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalyst2×HCID 702EthanolSolvent

Procedure

410.0 g of 2,4-di-tert-butylphenol are hydrogenated in 820 ml of ethanol under 40 bar at 60° C. using 20 g of rhodium on carbon (5%) for 21 hours. To complete the reaction, the pressure is raised to 120 bar, a further 10 g of rhodium on carbon (5%) are added, and the hydrogenation is continued at 100° C. for 17 hours. The catalyst is filtered off, the solvent is distilled off under reduced pressure, and the residue is distilled off under high vacuum to leave 380.43 g (91% of theory) of 2,4-di-tert-butylcyclohexanone (mixed isomers) as a colourless liquid. Boiling point: 79-86° C./0.22 mbar.

Workup

  1. customfor 21 hours
  2. customthe reaction
  3. temperaturethe pressure is raised to 120 bar
  4. filtrationThe catalyst is filtered off
  5. distillationthe solvent is distilled off under reduced pressure
  6. distillationthe residue is distilled off under high vacuum

Sources & evidence

ORD record
ord-1f2470bda4f04a2baa2ce6c00db94180
Source dataset
uspto-grants-2002_03
Patent number
US06355783B1

Linked notes

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