Acetic Anhydride → Limonene diepoxide

HRID 1881807Notes

Reaction equation

HRID 1881807 reaction equation
[CH3:1][C:2]1[CH2:7]C[C@@H:5](C(C)=C)[CH2:4][CH:3]=1.C([O-])([O-])=[O:12].C([O-])([O-])=O.OO.OO.OO.[Na+].[Na+].[Na+].[Na+].[C:29]([O:32][C:33](=O)[CH3:34])(=O)[CH3:30]>C(OCCCC)(=O)C>[CH3:30][C:29]12[O:32][CH:33]1[CH2:34][CH:3]([C:2]1([CH3:1])[O:12][CH2:7]1)[CH2:4][CH2:5]2

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 159762Sodium percarbonateHCID 440917(+)-Limonene

Product 1

HCID 232703Limonene diepoxideYield 99%

Reagents, catalysts & solvents 1

HCID 31272Butyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Limonene (1.36 g, 10 mmol) was dissolved in butyl acetate (25 ml), and a composition containing sodium percarbonate (10.5 g, 66.7 mmol) and acetic anhydride (10.2 g, 100 mmol) was added thereto. The mixture was stirred at 60° C. After 12 hours, the reaction solution was washed with water to thereby completely remove acetic acid and sodium acetate, which were generated as by-products, and the remaining H2O2. Butyl acetate was distilled off from the organic phase by distillation, and as a result, 1.66 g (99% yields) of limonene diepoxide with a GC purity of 100% was obtained.

Workup

  1. additionwas added
  2. washthe reaction solution was washed with water to thereby completely remove acetic acid and sodium acetate, which
  3. distillationButyl acetate was distilled off from the organic phase by distillation

Sources & evidence

ORD record
ord-756f02b83b414ff8a3f468c19c9d140b
Source dataset
uspto-grants-2012_11
Patent number
US08318958B2

Reaction notes

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