Sodium Carbonate → 3-(tert-Butyl)cyclohexanone

HRID 260021Notes

Reaction equation

HRID 260021 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[H][H]>[Pd]>[C:1]([CH:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11450Phenol, 3-(1,1-dimethylethyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 1367503-(tert-Butyl)cyclohexanoneYield 75.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

300 g (2 mol) of 3-tert.butylphenol are hydrogenated in the presence of 3 g of palladium-on-active charcoal 5% and 3 g of anhydrous sodium carbonate at 0.15-0.3 bar hydrogen over-pressure and 115° C. In an autoclave for 21 hours. The mixture is then filtered over Celite. The Celite is washed with ether and the solution is evaporated. In this manner there are obtained 310.8 g of crude product, namely 1.5% trans-tert.butylcyclohexanol, 3.5% cis-tert.butylcyclohexanol, 86% 3-tert.butylcyclohexanone and 7.6% 3-tert.butylphenol. This product can be purified by distillation. There are obtained 232 g (75%) of 3-tert.butylcyclohexanone, b.p. 75°-76° C., 2 mbar (olfactorily acceptable, purity 94%) in addition to 11.3 g (3.6%) of impure material (purity 92%).

Workup

  1. filtrationThe mixture is then filtered over Celite
  2. washThe Celite is washed with ether
  3. customthe solution is evaporated
  4. customIn this manner there are obtained 310.8 g of crude product, namely 1.5% trans-tert.butylcyclohexanol, 3.5% cis-tert.butylcyclohexanol, 86% 3-tert.butylcyclohexanone and 7.6% 3-tert.butylphenol
  5. distillationThis product can be purified by distillation

Sources & evidence

ORD record
ord-02d398f8c6c14e9992bdc4f54d2c71d5
Source dataset
uspto-grants-1996_06
Patent number
US05525589

Reaction notes

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