Acetic Anhydride → Limonene diepoxide

HRID 1881809

Reaction equation

HRID 1881809 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][C@@H:5]([C:8]([CH3:10])=[CH2:9])[CH2:4][CH:3]=1.B1([O-])OO1.[OH2:15].[OH2:16].O.O.[Na+].C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1>[CH3:1][C:2]12[O:15][CH:7]1[CH2:6][CH:5]([C:8]1([CH3:10])[O:16][CH2:9]1)[CH2:4][CH2:3]2

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 440917(+)-LimoneneHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 232703Limonene diepoxideYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Limonene (1.36 g, 10 mmol) was dissolved in toluene (25 ml), and a composition containing sodium perborate tetrahydrate (15.4 g, 100 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. Toluene 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 98% 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. distillationToluene was distilled off from the organic phase by distillation

Sources & evidence

ORD record
ord-00efc152fb354a6f9f53c092d9d2df38
Source dataset
uspto-grants-2012_11
Patent number
US08318958B2

Linked notes

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