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

HRID 969165Notes

Reaction equation

HRID 969165 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 throught 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
  2. customfor 10 minutes
  3. additionMethyl sulfide was added
  4. washThe mixture was washed with water and brine successively
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bba1c8584d0d4fada9bf87ccf438e9ff
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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