Acetic Anhydride → Limonene diepoxide
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]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Limonene (1.36 g, 10 mmol) was dissolved in butyl acetate (25 ml), and a composition containing sodium percarbonate (6.0 g, 38.1 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, 1.63 g (97% yields) of limonene diepoxide with a GC purity of 97% were obtained.
Workup
- additionwas added
- washthe reaction solution was washed with water to thereby completely remove acetic acid and sodium acetate, which
- distillationButyl acetate was distilled off from the organic phase by distillation
Sources & evidence
- ORD record
- ord-ee42dbb0025f4eb69d6c6a9cc16241ea
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318958B2
Reaction notes
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