Oxalyl chloride → 5-Acetyl-2-ethoxybenzoyl chloride

HRID 21956Notes

Reaction equation

HRID 21956 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[C:7]([C:10]1[CH:11]=[CH:12][C:13]([O:19][CH2:20][CH3:21])=C([CH:18]=1)C(O)=O)(=[O:9])[CH3:8]>ClCCl.CN(C)C=O>[C:7]([C:10]1[CH:11]=[CH:12][C:13]([O:19][CH2:20][CH3:21])=[C:1]([CH:18]=1)[C:2]([Cl:4])=[O:3])(=[O:9])[CH3:8]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 185365885-Acetyl-2-ethoxybenzoic acid

Product 1

HCID 212508125-Acetyl-2-ethoxybenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (3.66 g, 0.029 mol) was added dropwise to a stirred solution of 5-acetyl-2-ethoxybenzoic acid (3.0 g, 0.014 mol) in dichloromethane (15 ml) and dimethylformamide (0.1 ml). After 3 hours at room temperature, the solvent was removed by evaporation under vacuum and the residue azeotroped with hexane (3×30 ml) to give the title compound, which was used without further purification.

Workup

  1. customthe solvent was removed by evaporation under vacuum
  2. customthe residue azeotroped with hexane (3×30 ml)

Sources & evidence

ORD record
ord-a2a593b8d7bd4d9ba1d87309d78d039e
Source dataset
uspto-grants-1995_06
Patent number
US05426107

Reaction notes

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