tert-Butyl hydroperoxide → 3,5,5-TRIMETHYL-3-(t-BUTYLPEROXY)CYCLOHEXANONE

HRID 127869

Reaction equation

HRID 127869 reaction equation
[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([CH3:10])=[CH:3]1.[C:11]([O:15][OH:16])([CH3:14])([CH3:13])[CH3:12]>>[CH3:10][C:4]1([O:16][O:15][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:5][C:6]([CH3:8])([CH3:7])[CH2:9][C:2](=[O:1])[CH2:3]1

Participants

3

Reactant 2

HCID 6410tert-Butyl hydroperoxideHCID 6544Isophorone

Product 1

HCID 205704733,5,5-TRIMETHYL-3-(t-BUTYLPEROXY)CYCLOHEXANONE

Procedure

A reaction mixture of 62.2 g. (0.45 mole) of isophorone, 104 g. (0.9 mole) of 78% t-butyl hydroperoxide and 32.4 g. of Amberlyst 15® sulfonic acid type ion-exchange resin was stirred at 40° C. for 48 hours and at 50° C. for one hour. The ion-exchange resin was separated by filtration, the filtrate diluted with pentane and the pentane solution washed with water and sodium bisulfite solution. After drying over anhydrous magnesium sulfate, the pentane was removed under reduced pressure. The recovered product weighed 74.7 g. (72.8% of the calculated amount). The infrared spectrum had a strong absorption band in the 880 cm-1 region usually associated with t-butylperoxy groups. Iodometric assay showed the presence of active oxygen.

Workup

  1. additionA reaction mixture of 62.2 g
  2. customThe ion-exchange resin was separated by filtration
  3. additionthe filtrate diluted with pentane
  4. washthe pentane solution washed with water and sodium bisulfite solution
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe pentane was removed under reduced pressure

Sources & evidence

ORD record
ord-160264ca3b914a1bb4502961bd9a8e0b
Source dataset
uspto-grants-1981_03
Patent number
US04257985

Linked notes

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