Oxalyl chloride → 2-(3,4-Dichlorophenyl)acetyl chloride

HRID 484109Notes

Reaction equation

HRID 484109 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C(Cl)(=O)C([Cl:16])=O>ClCCl.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([Cl:16])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 798743,4-Dichlorophenylacetic acid

Product 1

HCID 27581492-(3,4-Dichlorophenyl)acetyl chlorideYield 95.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

3,4-Dichlorophenylacetic acid (76.8 g) was dissolved in dry dichloromethane (300 ml) and oxalyl chloride (52 g, 36 ml) was added to the solution obtained in one portion. The reaction mixture was protected from atmospheric moisture with a calcium chloride guard tube and stirred mechanically whilst dimethylformamide (3 drops) was added. The solution was stirred at ambient temperature for 18 hours and then evaporated under reduced pressure to give a yellow oil. Distillation in vacuo afforded 80.0 g of 3,4-dichlorophenylacetyle chloride, b.pt 97°-100°/0.6 mm, as a viscous pale yellow oil.

Workup

  1. customobtained in one portion
  2. customThe reaction mixture was protected from atmospheric moisture with a calcium chloride guard tube
  3. additionwas added
  4. customevaporated under reduced pressure
  5. customto give a yellow oil
  6. distillationDistillation in vacuo

Sources & evidence

ORD record
ord-a2d2e97ed92e4e9099ffc287fc0b432c
Source dataset
uspto-grants-1993_07
Patent number
US05229414

Reaction notes

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