Thionyl Chloride → 2-Cyano-3-phenylprop-2-enoyl chloride

HRID 1461188Notes

Reaction equation

HRID 1461188 reaction equation
[C:1]([C:3](=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4](O)=[O:5])#[N:2].S(Cl)([Cl:16])=O>C1C=CC=CC=1>[C:1]([C:3](=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([Cl:16])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 705342-Cyano-3-phenylprop-2-enoic acid

Product 1

HCID 540043722-Cyano-3-phenylprop-2-enoyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

100 ml of benzene was added to 17.3 grams of α-cyanocinnamic acid. 12 ml of thionyl chloride was added dropwise slowly thereto at ambient temperature. The temperature was elevated to 70° C. and the heating was continued until foaming ceased. Benzene and thionyl chloride were distilled off and the residue was dried thoroughly under reduced pressure.

Workup

  1. customat ambient temperature
  2. customwas elevated to 70° C.
  3. distillationBenzene and thionyl chloride were distilled off
  4. customthe residue was dried thoroughly under reduced pressure

Sources & evidence

ORD record
ord-bc1d7a05f5dd405cafd5e122f1785e63
Source dataset
uspto-grants-1991_12
Patent number
US05075009

Reaction notes

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