3,3-Diphenylacrylic acid → 3,3-Diphenylacryloyl chloride

HRID 1613303Notes

Reaction equation

HRID 1613303 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[C:7]1([C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][C:15](O)=[O:16])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[C:7]1([C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][C:15]([Cl:2])=[O:16])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 118263,3-Diphenylacrylic acidHCID 24819Phosphorus pentachloride

Product 1

HCID 112535443,3-Diphenylacryloyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.164 g of phosphorus pentachloride were added to 90 ml of a methylene chloride solution containing 4.485 g of 3,3-diphenylacrylic acid, which had previously been cooled at 0°-5° C. The reaction mixture was then stirred for one hour at room temperature, after which the solvent was distilled off under reduced pressure. The resulting residue was dissolved in 50 ml of toluene, and then the solvent was once again distilled off under reduced pressure. This procedure comprising dissolution and distillation was repeated once more. 3,3-Diphenylacryloyl chloride was obtained as a white solid. This crude product was immediately used in the next reaction.

Workup

  1. temperaturehad previously been cooled at 0°-5° C
  2. distillationafter which the solvent was distilled off under reduced pressure
  3. dissolutionThe resulting residue was dissolved in 50 ml of toluene
  4. distillationthe solvent was once again distilled off under reduced pressure
  5. dissolutionThis procedure comprising dissolution and distillation

Sources & evidence

ORD record
ord-6521cdaa9159414c9e835ab39d7a0edc
Source dataset
uspto-grants-1993_03
Patent number
US05192766

Reaction notes

Loading…