Oxalyl chloride → 4-(Chloromethyl)benzoyl chloride

HRID 353811

Reaction equation

HRID 353811 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[Cl:7][CH2:8][C:9]1[CH:17]=[CH:16]C(C(O)=O)=[CH:11][CH:10]=1>ClCCl.CN(C)C=O>[Cl:7][CH2:8][C:9]1[CH:17]=[CH:16][C:1]([C:2]([Cl:4])=[O:3])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 742344-(Chloromethyl)benzoic acid

Product 1

HCID 701364-(Chloromethyl)benzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (4.4 mL of 2M in chloroform, 8.8 mmol) was added to a suspension of 4-(chloromethyl)benzoic acid (1 g, 5.7 mmol) in dichloromethane. N,N-dimethylformamide (4 drops) was added to catalyze the reaction. After 1 hour analysis by HPLC indicated 100% clean conversion. The reaction mixture was concentrated under vacuum to provide 4-(chloromethyl)benzoyl chloride.

Workup

  1. customthe reaction
  2. concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-7cadaf82a2f04fe683c43460d0dc3fad
Source dataset
uspto-grants-2004_06
Patent number
US06756382B2

Linked notes

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