Water → Oxirane, (2,2-diphenylethyl)-

HRID 275463Notes

Reaction equation

HRID 275463 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH:9]=[CH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:25])C=1.O.S([O-])(O)=O.[Na+]>ClCCl>[C:1]1([CH:7]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:8][CH:9]2[O:25][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 118306504,4-Diphenyl-1-buteneHCID 23665763Sodium Bisulfite

Product 1

HCID 9991206Oxirane, (2,2-diphenylethyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.52 g of 4,4-diphenylbut-1-ene in 25 mL of dichloromethane at 0° C. was added 0.75 g of 50-60% by wt of m-chloroperbenzoic acid. The mixture was stirred at room temperature overnight, then heated at reflux for 1 hr. Water, 1 mL, and 0.25 g of sodium hydrogen sulfite were added to destroy the excess oxidizing agent. The organic layer was washed with water and dilute sodium hydrogen carbonate solution, dried, then concentrated in vacuo to give 0.5 g of 4,4-diphenylbut-1-ene oxide which is characterized by:

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hr
  3. customto destroy the excess oxidizing agent
  4. washThe organic layer was washed with water and dilute sodium hydrogen carbonate solution
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-353d6394b2b741dbb1bc3501b793114f
Source dataset
uspto-grants-1995_02
Patent number
US05393795

Reaction notes

Loading…