2,4-Dimethylbenzoic acid → 2,4-Dimethylbenzoyl chloride

HRID 1889004Notes

Reaction equation

HRID 1889004 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:15])=O>ClCCl.CN(C=O)C>[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:15])=[O:5]

Participants

5

Reactant 2

HCID 118972,4-Dimethylbenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 1408672,4-Dimethylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

2,4-Dimethylbenzoic acid (1.502 g, 10 mmol, commercially available from e.g. Sigma-Aldrich, Fluka or Alfa Aesar) in dichloromethane (DCM) (40 mL) was cooled to 0° C., before oxalyl chloride (0.963 mL, 11.00 mmol) and a few drops of DMF (cat.) were added. The solution was then stirred under argon for 3 hours. The solvent was then evaporated in vacuo and the remaining residue was azeotroped with toluene (2×20 mL) to yield the product in 1.639 g.

Workup

  1. additionwere added
  2. customThe solvent was then evaporated in vacuo
  3. customthe remaining residue was azeotroped with toluene (2×20 mL)
  4. customto yield the product in 1.639 g

Sources & evidence

ORD record
ord-7cc5dbc054534bf7b6530e493def18e4
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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