Hydrogen Peroxide → Benzamide

HRID 267263Notes

Reaction equation

HRID 267263 reaction equation
C12OC3CC([O:9]1)C(C=C3)C2.C(=O)(O)[O-].[K+].[C:16](#[N:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.OO>CO.C(Cl)Cl>[C:16]([NH2:23])(=[O:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 7505BenzonitrileHCID 516893Potassium BicarbonateHCID 53690519HCID 53690519, compound

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 165 mg of racemic 9,10-dioxatricyclo[4,3,1,03,8 ]dec-4-ene in 4 ml of methanol are added, with stirring and at room temperature 865 mg of potassium bicarbonate and 740 mg of benzonitrile. To this mixture are added at intervals of 8 hours 5 portions each of 0.3 ml of 30% hydrogen peroxide and stirring is continued for 10 hours. Methylene chloride (25 ml) is then added to the reaction mixture, which is washed with 2% sodium hydrogen carbonate solution, dried over sodium sulphate and concentrated. Benzamide which has formed is removed by crystallisation from methylene chloride/pentane. The residual oil can be used directly in the next reaction, or chromatographed on 22 g of basic aluminium oxide (activity level IV). Elution with petroleum ether/benzene (7:3) yields the racemic mixture of 4β,5β-epoxy-9,10-dioxatricyclo[4,3,1,03,8 ]decane of the formula ##SPC18##

Workup

  1. washis washed with 2% sodium hydrogen carbonate solution
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-03bace021e09452bbaee02314b6f0bee
Source dataset
uspto-grants-1976_03
Patent number
US03941813

Reaction notes

Loading…