Toluene → Limonene diepoxide

HRID 1881808Notes

Reaction equation

CC1CC[C@@H](C(C)=C)CC=1.C([O-])([O-])=[O:12].C([O-])([O-])=O.OO.OO.OO.[Na+].[Na+].[Na+].[Na+].[C:29]1(=O)[O:34][C:32](=O)[C:31]2=CC=CC=C12.[C:40]1([CH3:46])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>>[CH3:46][C:40]12[O:12][CH:45]1[CH2:44][CH:43]([C:32]1([CH3:31])[O:34][CH2:29]1)[CH2:42][CH2:41]2

Participants

Reactant 4

HCID 1140Toluene

HCID 6811Phthalic Anhydride

HCID 159762Sodium percarbonate

HCID 440917(+)-Limonene

Product 1

HCID 232703Limonene diepoxideYield 99%

Conditions

Temperature: 60 °C

Procedure

Limonene (1.36 g, 10 mmol) was dissolved in toluene (25 ml), and a composition containing sodium percarbonate (10.5 g, 66.7 mmol) and phthalic anhydride (14.8 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 phthalic acid, sodium phthalate, and disodium phthalate, which were generated as by-products, and the remaining H2O2. Toluene was distilled off from the organic phase by distillation, and as a result, 1.66 g (99% yields) of limonene diepoxide with a GC purity of 100% was obtained.

Workup

additionwas added
washthe reaction solution was washed with water to thereby completely remove phthalic acid, sodium phthalate, and disodium phthalate, which
distillationToluene was distilled off from the organic phase by distillation

Sources & evidence

ORD record: ord-8e5798d827c14d6aa5c2a1d2210861c0
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318958B2

Reaction notes

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