Sodium Carbonate → Cyclohexanone, 2-methyl-5-(1-methylethyl)-

HRID 971603

Reaction equation

HRID 971603 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][C@@H:5]([CH:8]([CH3:10])[CH3:9])[C@@H:4]([OH:11])[CH:3]=1.[CH3:12][C:13]1[CH2:18][CH2:17][C@H:16]([CH:19]([CH3:21])[CH3:20])[C@@H:15]([OH:22])[CH:14]=1.[Ba].[C:24](=[O:27])([O-])[O-].[Na+].[Na+]>[Cr]([O-])([O-])=O.[Cu+2]>[CH3:1][C@H:2]1[CH2:3][C:4](=[O:11])[C@H:5]([CH:8]([CH3:10])[CH3:9])[CH2:6][CH2:7]1.[CH3:12][CH:13]1[CH2:14][C:15](=[O:22])[CH:16]([CH:19]([CH3:21])[CH3:20])[CH2:17][CH2:18]1.[CH3:1][CH:2]1[C:24](=[O:27])[CH2:6][CH:5]([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 85567cis-PiperitolHCID 855682-Cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-, (1R,6R)-rel-HCID 5355457Barium

Product 2

HCID 10362Cyclohexanone, 2-methyl-5-(1-methylethyl)-HCID 131711575Menthone isomenthone

Reagents, catalysts & solvents 1

HCID 178505374HCID 178505374, compoundCatalyst

Procedure

A pressure vessel was charged with 500 g of a mixture of alcohols containing 93.9 g of cis-piperitol, 136.45 g of trans-piperitol, and 187.,8 g of cis and trans-carvenols, 10 g of Girdler G-22 barium promoted copper chromite catalyst, and 10 g of sodium carbonate. The vessel was heated with stirring to 200°-240° C. for 2 hours. After cooling, the product was filtered and distilled to yield 210.5 g of menthone/isomenthone mixture and 147.3 g of carvomenthone. The menthones and carvomenthones were cleanly separated by distillation. The distillation residue containing piperitone and carvenone was hydrogenated at 60 psig hydrogen pressure and ambient temperature using 2% Raney nickel catalyst. Distillation of the hydrogenated product yielded an additional 8.2 g of mentone and 5.3 g of carvomenthone.

Workup

  1. temperatureThe vessel was heated
  2. temperatureAfter cooling
  3. filtrationthe product was filtered
  4. distillationdistilled

Sources & evidence

ORD record
ord-d524c09a34b1404b8d60944b7fb8a679
Source dataset
uspto-grants-1979_07
Patent number
US04160786

Linked notes

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