Cyclohexane → Cyclohexanone

HRID 1576891Notes

Reaction equation

HRID 1576891 reaction equation
C1CCCCC1.N[C:8]1([O:17]O)[CH2:13][CH:12]([CH3:14])[CH2:11][C:10]([CH3:16])([CH3:15])[CH2:9]1.S([O-])([O-])(=O)=O.[Mg+2]>S(=O)(=O)(O)O.C(O)C>[C:8]1(=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[CH3:14][CH:12]1[CH2:11][C:10]([CH3:16])([CH3:15])[CH2:9][C:8](=[O:17])[CH2:13]1

Participants

7

Reactant 3

HCID 8078CyclohexaneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 215101831-Amino-3,3,5-trimethylcyclohexyl hydroperoxide

Product 2

HCID 7967CyclohexanoneHCID 133983,3,5-Trimethylcyclohexanone

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 702EthanolSolvent

Procedure

To a stirred mixture of cyclohexane (19.6 g.) and ethanol (50 c.c.), kept at or below 0°C, was added 1-amino-3,3,5-trimethylcyclohexyl hydroperoxide (17.3 g., 78% pure); solution was complete in ca. 10 min. To the solution was added conc. sulphuric acid (3 drops) and magnesium sulphate and the mixture was stored at 0°C for 3 days. The solid was filtered off, the filtrate washed with water, dried and distilled, to give cyclohexanone, dihydroisophorone and a fraction (11.5 g.), b.p. 90° - 100°C at 0.02 mm. Hg., peroxide equivalent 179. By mass spectroscopy the product was shown to contain the unsymmetrical peroxide 1,1'-amino-3,3,5-trimethylcyclohexylamine. ##SPC65##

Workup

  1. custombelow 0°C
  2. waitthe mixture was stored at 0°C for 3 days
  3. filtrationThe solid was filtered off
  4. washthe filtrate washed with water
  5. customdried
  6. distillationdistilled

Sources & evidence

ORD record
ord-e7072115860846da83da59fe4645ea52
Source dataset
uspto-grants-1976_09
Patent number
US03983142

Reaction notes

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