Hydrogen Peroxide → HCID 12272042, compound

HRID 225151Notes

Reaction equation

HRID 225151 reaction equation
[CH:1](=[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(=O)(O)[O-:20].[K+].OO>CO>[CH2:2]([CH:1]1[O:20][C:8]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 348771diethyl 2-heptylidenepropanedioateHCID 516893Potassium Bicarbonate

Product 1

HCID 12272042HCID 12272042, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 31 g of diethyl heptylidenepropanedioate (B. Wojcik and H. Adkins, J. Am. Chem. Soc., 56, 2424 (1934), prepared by the method of A. C. Cope and K. E. Hoyle, J. Am. Chem. Soc., 63, 733 (1941)), 5 g of potassium bicarbonate and 17 g of 30% hydrogen peroxide in 200 ml of methanol was stirred for two hours at 40° C., then allowed to stand at 20° C. for 16 hours. The mixture then was concentrated to 50 ml; 100 ml of water was added and the solution was extracted with two 50-ml volumes of methylene chloride. The solvent was evaporated to give a colorless liquid, which was vacuum distilled to give diethyl 3-hexyloxiranedicarboxylate (2A), bp: 117°-126° C. at 0.1 Torr.

Workup

  1. custom, 56, 2424 (1934), prepared by the method of A
  2. concentrationThe mixture then was concentrated to 50 ml
  3. addition100 ml of water was added
  4. extractionthe solution was extracted with two 50-ml volumes of methylene chloride
  5. customThe solvent was evaporated
  6. customto give a colorless liquid, which
  7. distillationdistilled

Sources & evidence

ORD record
ord-29d097ad048d4d0a9603adf09c781b42
Source dataset
uspto-grants-1980_11
Patent number
US04235923

Reaction notes

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