Dichloromethane → 1-(4-Formylphenyl)cyclopropane-1-carbonitrile

HRID 504364Notes

Reaction equation

HRID 504364 reaction equation
[O:1]=[O+][O-].[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:15]#[N:16])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=C.C(Cl)Cl>>[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:15]#[N:16])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=[O:1]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24823OzoneHCID 666626411-(4-Vinylphenyl)cyclopropanecarbonitrile

Product 1

HCID 866022841-(4-Formylphenyl)cyclopropane-1-carbonitrile

Procedure

Ozone was bubbled through a solution of 1-(4-vinylphenyl)cyclopropanecarbonitrile (1.8 g, 0.011 mol) in methylene chloride (40 mL, 0.6 mol) at −78° C. until a blue color appeared and then nitrogen was bubbled through the solution for 10 minutes. Methyl sulfide was added and the mixture was stirred overnight. The mixture was washed with water and brine successively, dried, and concentrated to give the desired product.

Workup

  1. customnitrogen was bubbled through the solution for 10 minutes
  2. additionMethyl sulfide was added
  3. washThe mixture was washed with water and brine successively
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-372bdad23fed4335996345f99e0a1da6
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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