Dimethylformamide → (2E)-3-(4-Chlorophenyl)acryloyl chloride

HRID 6797Notes

Reaction equation

HRID 6797 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([OH:12])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:16])=O.CN(C)C=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([Cl:16])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 6377974-Chlorocinnamic acid

Product 1

HCID 11252649(2E)-3-(4-Chlorophenyl)acryloyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2E)-3-(4-chlorophenyl)prop-2-enoic acid (2.0 g, 11 mmol) in 50 mL methylene chloride was added oxalyl chloride (1.05 mL, 12.1 mmol) and N,N-dimethylformamide (0.05 mL, 0.6 mmol). The resulting mixture was stirred at r.t. for 6 h. The solvent was removed under vacuum. The resulting solid was diluted with hexanes and the solvent removed under vacuum to provide an off-white solid which was used without further purification.

Workup

  1. customThe solvent was removed under vacuum
  2. additionThe resulting solid was diluted with hexanes
  3. customthe solvent removed under vacuum
  4. customto provide an off-white solid which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-98ba0a4789094cd8bd645b484b6e0ba8
Source dataset
uspto-grants-2006_08
Patent number
US07084156B2

Reaction notes

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