Toluene → HCID 53717999, compound

HRID 2073651Notes

Reaction equation

HRID 2073651 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([CH:8]=[CH:9][C:10]#[N:11])=[CH:6][CH:5]=1)(O)=[O:2].S(Cl)([Cl:16])=O.C1(C)C=CC=CC=1>CN(C)C=O>[Cl:16][C:1]([C:4]1[CH:13]=[CH:12][C:7]([CH:8]=[CH:9][C:10]#[N:11])=[CH:6][CH:5]=1)=[O:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 3041687HCID 3041687, compound

Product 1

HCID 53717999HCID 53717999, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14.3 g (83 mmols) of 4-carboxycinnamonitrile, 11.9 g (100 mmols) of thionyl chloride, 100 ml of toluene and 0.18 ml of N,N-dimethylformamide are boiled under reflux for 15 minutes and then evaporated. Recrystallising the residue twice from carbon tetrachloride gives 7.7 g (48% of theory) of 4-chloroformylcinnamonitrile in the form of yellow crystals; melting point 161.0° C.

Workup

  1. temperatureunder reflux for 15 minutes
  2. customevaporated
  3. customRecrystallising the residue twice from carbon tetrachloride

Sources & evidence

ORD record
ord-c8c38b71060a4cc5be7b230665c31303
Source dataset
uspto-grants-1990_04
Patent number
US04918215

Reaction notes

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