Peracetic Acid → HCID 14607966, compound

HRID 724751Notes

Reaction equation

HRID 724751 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][C:5]1[CH2:9][CH2:8][CH2:7][CH:6]=1.C([O-])(=[O:13])C.[Na+].C(OO)(=O)C>C(Cl)(Cl)Cl.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH:5]1[CH2:9][CH:8]2[O:13][CH:7]2[CH2:6]1

Participants

6

Reactant 3

HCID 6585Peracetic AcidHCID 517045Sodium AcetateHCID 12282108Methyl (cyclopent-1-en-1-yl)acetate

Product 1

HCID 14607966HCID 14607966, compoundYield 424.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Conditions

Temperature
35 °C

Procedure

43.46 g (0.31 mol) of cyclopentenylacetic acid methyl ester are dissolved in 80 ml of chloroform. After the addition of 4 g of sodium acetate, 82.51 g of a 40% solution of peracetic acid in acetic acid are added dropwise thereto, with stirring, the temperature being maintained at about 35° C. The reaction mixture is then stirred for a further 5 hours at 35° C. The reaction mixture is extracted with 5% sodium hydrogen carbonate solution and then twice with water. The organic phase is then separated off and dried and residual peroxide is destroyed with sodium sulfite. After distillation of the organic phase there are obtained 32.3 g of 3,4-epoxycyclopentylacetic acid methyl ester (66.5% of theory).

Workup

  1. additionare added dropwise
  2. stirringThe reaction mixture is then stirred for a further 5 hours at 35° C
  3. extractionThe reaction mixture is extracted with 5% sodium hydrogen carbonate solution
  4. customThe organic phase is then separated off
  5. customdried
  6. customresidual peroxide is destroyed with sodium sulfite
  7. distillationAfter distillation of the organic phase there

Sources & evidence

ORD record
ord-b52ae5b3f873495394226c06ff7b3f79
Source dataset
uspto-grants-1998_01
Patent number
US05705316

Reaction notes

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