Oxalyl chloride → 3-Vinylbenzoyl chloride

HRID 660478Notes

Reaction equation

HRID 660478 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](O)=[O:7])=[CH2:2].C(Cl)(=O)C([Cl:15])=O>C(Cl)Cl.CN(C=O)C>[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([Cl:15])=[O:7])=[CH2:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 44382313-Vinylbenzoic Acid

Product 1

HCID 125414943-Vinylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-vinylbenzoic acid (1.0 g, 6.75 mmol) in CH2Cl2 (20 mL) is added oxalyl chloride (2.35 mL, 3.42 g, 26.9 mmol) and 1 drop of DMF. After 2 h the solvent is removed under reduced pressure and the residue is redissolved in CH2Cl2 and concentrated again (4×) to afford the title compound which is used without further purification.

Workup

  1. customAfter 2 h the solvent is removed under reduced pressure
  2. dissolutionthe residue is redissolved in CH2Cl2
  3. concentrationconcentrated again (4×)

Sources & evidence

ORD record
ord-ec286da911a8472085bbe4379e364a17
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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