Dimethylformamide → 2,3-Dimethylbenzoyl chloride

HRID 1984740Notes

Reaction equation

HRID 1984740 reaction equation
[CH3:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CN(C)C=O.C(Cl)(=O)C([Cl:20])=O>C1(C)C=CC=CC=1.C(Cl)(=O)C(Cl)=O>[CH3:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:20])=[O:5]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 117822,3-Dimethylbenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 28008992,3-Dimethylbenzoyl chlorideYield 89.9%

Reagents, catalysts & solvents 2

HCID 65578Oxalyl chlorideCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 2,3-dimethylbenzoic acid (2.0 kg, 13.2 mol) in toluene (20 L) was added N,N-dimethylformamide (20 ml), followed by oxalyl chloride (2.0 kg, 15.6 mol) at room temperature. The reaction mixture was stirred at room temperature for 4 h and monitored by thin layer chromatography. If necessary, excess oxalyl chloride (25 g) was added until no starting material was observed. Excess toluene and oxalyl chloride were removed by distillation under vacuum at temperatures below 70° C. To the residue was added toluene (150 ml) and the mixture was again concentrated in vacuo to give 2,3-dimethylbenzoyl chloride (2.0 kg).

Workup

  1. customExcess toluene and oxalyl chloride were removed by distillation under vacuum at temperatures below 70° C
  2. additionTo the residue was added toluene (150 ml)
  3. concentrationthe mixture was again concentrated in vacuo

Sources & evidence

ORD record
ord-78e21aa8ab1245a28ec2684cdd152fa0
Source dataset
uspto-grants-2009_06
Patent number
US07544706B2

Reaction notes

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