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

HRID 846545Notes

Reaction equation

HRID 846545 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-f2b1c9ec8d6e43aba5f66b1550d5fea1
Source dataset
uspto-grants-1992_08
Patent number
US05137638

Reaction notes

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