Hydrogen Peroxide → Cyclohexanone, trimethyl-

HRID 268116

Reaction equation

HRID 268116 reaction equation
[OH:1]O.[OH-].[Na+].C[C:6]1[CH2:11][CH2:10][CH2:9][C:8]([CH3:13])([CH3:12])[C:7]=1[CH:14]=O.O>CO.S(=O)(=O)(O)O>[CH3:14][CH:7]1[CH2:6][CH2:11][CH2:10][C:9](=[O:1])[C:8]1([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 9895beta-CyclocitralHCID 14798Sodium Hydroxide

Product 1

HCID 3016570Cyclohexanone, trimethyl-

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

110 ml of a solution of 30 % H2O2 followed by 28 ml of a 6N aqueous solution of NaOH were added dropwise, while stirring and within 45 minutes and 15 minutes, respectively, to a cooled solution (0°-5°) of 40 g of β-cyclocitral (0.26 mole) in 300 ml of methanol which had been acidified beforehand with 40 drops of concentrated sulphuric acid. The reaction mixture was then kept at room temperature for 3 days, while stirring. After having added water thereto, the said mixture was extracted three times with ether and the combined organic extracts were subjected to the usual treatments of washing (water), drying (MgSO4) and concentration. There were obtained 21.5 g of trimethyl-cyclohexanone by fractional distillation; b.p. 66°-69°/12 Torr (66 %).

Workup

  1. additionwere added dropwise
  2. waitThe reaction mixture was then kept at room temperature for 3 days
  3. stirringwhile stirring
  4. extractionthe said mixture was extracted three times with ether
  5. washof washing (water)
  6. customdrying
  7. concentration(MgSO4) and concentration

Sources & evidence

ORD record
ord-32828b8fe14547549316118173a6a1c0
Source dataset
uspto-grants-1976_03
Patent number
US03946078

Linked notes

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