1-(4-Methylcyclohexyl)propan-1-ol → 4-Methylcyclohexyl ethyl ketone

HRID 2227566Notes

Reaction equation

HRID 2227566 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH:8]([OH:11])[CH2:9][CH3:10])[CH2:4][CH2:3]1>C(OC)(C)(C)C.O.OS(O)(=O)=O>[CH2:9]([C:8]([CH:5]1[CH2:4][CH2:3][CH:2]([CH3:1])[CH2:7][CH2:6]1)=[O:11])[CH3:10]

Participants

5

Reactant 1

HCID 184743551-(4-Methylcyclohexyl)propan-1-ol

Product 1

HCID 184743574-Methylcyclohexyl ethyl ketoneYield 74.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1118Sulfuric AcidSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
22.5 °C

Procedure

A solution of 44 g (0.3 mol) of the alcohol of Example 1 in 200 ml of methyl tert-butyl ether (MTBE) was treated at not more than 20° C. with a solution of 42.9 g of Na2Cr2O7*2H2O in 210 ml of water and 35 ml of concentrated H2SO4. After the mixture had been stirred for approximately 16 hours at 20-25° C., the phases were separated and the aqueous phase was extracted with MTBE. After washing with water and drying, the combined organic phases [lacuna] distilled. The distillation gave 34.3 g of 4-methylcyclohexyl ethyl ketone as a colorless oil of b.p.50 of 114-116° C. According to 13C NMR analysis, the ratio between the cis and trans isomers in the mixture amounted to approximately 30:70.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with MTBE
  3. washAfter washing with water
  4. customdrying
  5. distillationthe combined organic phases [lacuna] distilled
  6. distillationThe distillation

Sources & evidence

ORD record
ord-748c5cb77b92493fb0f1b7158680e7ed
Source dataset
uspto-grants-2002_07
Patent number
US06414031B1

Reaction notes

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