Oxalyl chloride → 2-Ethyl-6-methylbenzoyl chloride

HRID 1936484Notes

Reaction equation

HRID 1936484 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:4]=1[C:5](O)=[O:6])[CH3:2].C(Cl)(=O)C([Cl:16])=O>ClCCl.CN(C=O)C>[CH2:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:4]=1[C:5]([Cl:16])=[O:6])[CH3:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 120442292-Ethyl-6-methylbenzoic acid

Product 1

HCID 223820492-Ethyl-6-methylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-ethyl-6-methylbenzoic acid (49 mg, 0.30 mmol) in dichloromethane (3 mL) containing DMF (1 drop) was treated with oxalyl chloride (0.14 mL, 1.6 mmol) and the mixture was stirred for 15 h. The mixture was concentrated, azeotroping with toluene to remove traces of oxalyl chloride and the residue was used directly in the next step.

Workup

  1. concentrationThe mixture was concentrated
  2. customazeotroping with toluene
  3. customto remove traces of oxalyl chloride

Sources & evidence

ORD record
ord-8863ec9453634770aa1fdd50a41a75a2
Source dataset
uspto-grants-2002_05
Patent number
US06388084B1

Reaction notes

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