Dicyclopentadiene → Dicyclopentadiene dioxide

HRID 1881810Notes

Reaction equation

HRID 1881810 reaction equation
[CH2:1]1[CH:5]2[CH:6]3[CH:10]=[CH:9][CH:8]([CH:4]2[CH:3]=C1)[CH2:7]3.[C:11]([O-:14])([O-])=O.C([O-])([O-])=[O:16].OO.OO.OO.[Na+].[Na+].[Na+].[Na+].C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1>[CH2:7]1[CH:6]2[CH:10]3[O:16][CH:9]3[CH:8]1[CH:4]1[CH:5]2[CH:1]2[O:14][CH:11]2[CH2:3]1

Participants

5

Reactant 3

HCID 6492DicyclopentadieneHCID 7918Acetic AnhydrideHCID 159762Sodium percarbonate

Product 1

HCID 6673Dicyclopentadiene dioxideYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Dicyclopentadiene (1.32 g, 10 mmol) was dissolved in toluene (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. Toluene was distilled off from the organic phase by distillation, and as a result, 1.62 g (99% yields) of dicyclopentadiene 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. distillationToluene was distilled off from the organic phase by distillation

Sources & evidence

ORD record
ord-2224e70288f943488aa7d9bf11c59547
Source dataset
uspto-grants-2012_11
Patent number
US08318958B2

Reaction notes

Loading…