4-Vinylbenzoic acid → 4-Vinylbenzoyl chloride

HRID 583438

Reaction equation

HRID 583438 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1)=[CH2:2].C(Cl)(=O)C([Cl:15])=O>C1C=CC=CC=1>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:15])=[O:8])=[CH:5][CH:4]=1)=[CH2:2]

Participants

4

Reactant 2

HCID 140984-Vinylbenzoic acidHCID 65578Oxalyl chloride2×

Product 1

HCID 110520284-Vinylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a clean round bottom flask with an argon atmosphere and equipped with a magnetic stir bar is added para-vinyl benzoic acid (10 g, 0.067 mole) which is suspended in benzene (25 ml). Oxalyl chloride (25 g, 0.197 mole) is added to the flask. The mixture is stirred for 8 hours and continuously flushed with a continuous stream of argon to purge the system of the gases generated during the reaction. Solvent and excess oxalyl chloride is stripped off under vacuum. Finally, the product is distilled under vacuum to yield para-vinyl benzoyl chloride. Approximately 90% of the theoretical yield is obtained.

Workup

  1. customTo a clean round bottom flask with an argon atmosphere and equipped with a magnetic stir bar
  2. customcontinuously flushed with a continuous stream of argon
  3. customto purge the system of the gases
  4. customgenerated during the reaction
  5. distillationFinally, the product is distilled under vacuum

Sources & evidence

ORD record
ord-401d8099b2454290a09de4fe33b1af82
Source dataset
uspto-grants-1999_07
Patent number
US05929173

Linked notes

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