Hydrogen Peroxide → 1,3,3-Trimethyl-7-oxabicyclo-[4.1.0]heptane-2,5-dione

HRID 436975Notes

Reaction equation

HRID 436975 reaction equation
[OH-:1].[Na+].[CH3:3][C:4]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[CH2:7][C:6](=[O:13])[CH:5]=1.OO.O>CO>[CH3:3][C:4]12[O:1][CH:5]1[C:6](=[O:13])[CH2:7][C:8]([CH3:12])([CH3:11])[C:9]2=[O:10]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 62374Ketoisophorone

Product 1

HCID 38532541,3,3-Trimethyl-7-oxabicyclo-[4.1.0]heptane-2,5-dioneYield 81.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2 ml of a 6N aqueous solution of NaOH have been added during a period of 15 minutes at 15° C. to a mixture of 3,5,5-trimethyl-cyclohex-2-en-1,4-dione (3.7 g) and hydrogen hydroperoxide (8.3 ml of a 30 % solution) in 27 ml of methanol. The mixture was kept under stirring during 3 hours at 20°-25° C., treated with water and extracted with ether. The combined organic extracts were washed with water until neutrality, dried over MgSO4 and evaporated. 3.33g (81.5%) of the desired product, b.p. 40° C./0.001 Torr, were thus obtained.

Workup

  1. extractionextracted with ether
  2. washThe combined organic extracts were washed with water until neutrality
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-b2169ef75f574b8f97ef94bfbc6409d0
Source dataset
uspto-grants-1977_06
Patent number
US04029107

Reaction notes

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