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

HRID 557901Notes

Reaction equation

HRID 557901 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-f3f56dd282544cfcaf989f549953b5d8
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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