Dimethylformamide → 3-Phenylprop-2-enoyl chloride

HRID 617005Notes

Reaction equation

HRID 617005 reaction equation
[CH:1]([C:9]([OH:11])=O)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CN(C)C=O.S(Cl)([Cl:19])=O>>[CH:1]([C:9]([Cl:19])=[O:11])=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 87842-Propenoic acid, 3-phenyl-HCID 24386Thionyl Chloride

Product 1

HCID 660233-Phenylprop-2-enoyl chloride

Procedure

The styrene carboxylic acid copolymer (20.0g) from example 7(b) was refluxed with stirring for 2 hours in thionyl chloride (300 ml.) containing N,N-dimethylformamide (3.0 ml.). After cooling to room temperature the mixture was filtered and the polymer washed with chloroform (5 × 100 ml., containing 2% v/v ethanol): and dried in vacuo at 40° to constant weight. The title polymer (21.80g) exhibited ν max (Nujol) 1770 and 1738 cm-1 (C=O) and was yellow-green in colour.

Workup

  1. filtrationwas filtered
  2. washthe polymer washed with chloroform (5 × 100 ml
  3. addition, containing 2% v/v ethanol): and
  4. customdried in vacuo at 40° to constant weight

Sources & evidence

ORD record
ord-c873e4c6f4ff43fd89745b02cc327156
Source dataset
uspto-grants-1978_02
Patent number
US04076913

Reaction notes

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