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

HRID 1287172Notes

Reaction equation

HRID 1287172 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. IR: 1715 cm-1 ; MS: M+ = 168; m/e: 56 NMR (CCl4) : 1.05 (3H,s); 1.25 (3H,s); 1.50 (3H,s); 2.08 (1H,d, J=13 cps); 3.09 (1H,d, J=13 cps); 3.47 (1H,s) δ ppm.

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-a26e1392c01e41c6bba5d28d2d0d8cc7
Source dataset
uspto-grants-1976_10
Patent number
US03983885

Reaction notes

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