Oxalyl chloride → 2-Methyl-6-(propan-2-yl)benzoyl chloride

HRID 1936487Notes

Reaction equation

HRID 1936487 reaction equation
[CH3:1][CH:2]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:5]=1[C:6](O)=[O:7])[CH3:3].C(Cl)(=O)C([Cl:17])=O>ClCCl.CN(C=O)C>[CH3:1][CH:2]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:5]=1[C:6]([Cl:17])=[O:7])[CH3:3]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 22382029HCID 22382029, compound

Product 1

HCID 223820312-Methyl-6-(propan-2-yl)benzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(1-methylethyl)-6-methylbenzoic acid (64 mg, 0.35 mmol) in dichloromethane (3 mL) containing DMF (2 drops) was treated with oxalyl chloride (0.16 mL, 1.8 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-ae01fd8e88f64d4b81ba91d407891daa
Source dataset
uspto-grants-2002_05
Patent number
US06388084B1

Reaction notes

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