Dimethylformamide → 2,3-Dimethylbenzoyl chloride

HRID 1169963Notes

Reaction equation

HRID 1169963 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-95826f735ea64811942c6169a01afd6c
Source dataset
uspto-grants-2010_11
Patent number
US07825149B2

Reaction notes

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