Hydrogen Peroxide → 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide

HRID 1361710Notes

Reaction equation

HRID 1361710 reaction equation
[CH2:1]([N:4]1[C:13](=[O:14])[CH:8]2[CH2:9][CH:10]=[CH:11][CH2:12][CH:7]2[C:5]1=[O:6])[CH:2]=[CH2:3].[Na].[OH:16]O>S([O-])(O)(=O)=O.C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.NCP(=O)(O)O>[O:16]1[CH:11]2[CH:10]1[CH2:9][CH:8]1[C:13](=[O:14])[N:4]([CH2:1][CH:2]=[CH2:3])[C:5](=[O:6])[CH:7]1[CH2:12]2

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 5360545SodiumHCID 13184973N-allyl-4-cyclohexene-1,2-dicarboximide

Product 1

HCID 252422084,5-epoxy-N-allylcyclohexane-1,2-dicarboximide

Reagents, catalysts & solvents 2

HCID 14017(Aminomethyl)phosphonic acidCatalystHCID 10939560Methyltricaprylylammonium bisulfateCatalyst

Procedure

100.0 g of N-allyl-4-cyclohexene-1,2-dicarboximide, 2.44 g of methyltrioctylammonium hydrogen sulfate, 3.45 g of sodium tungstenate dihydrate and 0.58 g of aminomethylphosphonic acid were charged into a 500 mL three-mouth flask provided with a reflux condenser, thermometer, stirring apparatus, dropping funnel and oil bath. After heating using the oil bath maintained at a temperature of 90° C., 80 ml of 30% aqueous hydrogen peroxide were dropped in over the course of 180 minutes through the dropping funnel followed by aging for 4 hours. After cooling with an ice bath and removing the excess hydrogen peroxide with 300 ml of saturated aqueous sodium thiosulfate solution, the reaction mixture was extracted twice with 200 ml of ethyl acetate. The resulting ethyl acetate solution was dried overnight with anhydrous sodium sulfate followed by removing the solvent ethyl acetate using a rotary evaporator and purifying by column chromatography using a column packed with 25% aqueous silica gel to obtain 78.9 g of 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide.

Workup

  1. customprovided with a reflux condenser
  2. temperatureAfter heating
  3. additionwere dropped in over the course of 180 minutes through the dropping funnel
  4. temperatureAfter cooling with an ice bath
  5. customremoving the excess hydrogen peroxide with 300 ml of saturated aqueous sodium thiosulfate solution
  6. extractionthe reaction mixture was extracted twice with 200 ml of ethyl acetate
  7. dry with materialThe resulting ethyl acetate solution was dried overnight with anhydrous sodium sulfate
  8. customby removing the solvent ethyl acetate using
  9. customa rotary evaporator
  10. custompurifying by column chromatography

Sources & evidence

ORD record
ord-4475fcbe862e4f4590119d5b6903e8c6
Source dataset
uspto-grants-2011_02
Patent number
US07880018B2

Reaction notes

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