Water → Oxirane, [3-(4-chlorophenyl)propyl]-

HRID 467058Notes

Reaction equation

HRID 467058 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])=[CH:4][CH:3]=1.C(OO)(=[O:15])C.C([O-])(=O)C.[Na+].O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]2[O:15][CH2:12]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6585Peracetic AcidHCID 517045Sodium AcetateHCID 20082700HCID 20082700, compound

Product 1

HCID 11084791Oxirane, [3-(4-chlorophenyl)propyl]-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(4-chlorophenyl)pent-1-ene (43.2 g) in dichloromethane (400 mL) was added dropwise with stirring a mixture of 40% peracetic acid (200 mL) and sodium acetate (6.5 g). The resulting mixture was heated under reflux for 2 hours, cooled, and stirred with water (400 mL). The dichloromethane layer was separated, washed with dilute aqueous potassium carbonate until neutral, water, and dried (MgSO4) and evaporated to give 46.7 g of 5-(4-chlorophenyl)-1,2-epoxypentane as a colorless oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. customThe dichloromethane layer was separated
  5. washwashed with dilute aqueous potassium carbonate until neutral, water
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-fe1bcf22ef464c588e66cca42665a13c
Source dataset
uspto-grants-1992_10
Patent number
US05158949

Reaction notes

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