2-Methoxybenzoic acid → 2-Methoxybenzoyl chloride

HRID 398015Notes

Reaction equation

HRID 398015 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6].S(Cl)([Cl:14])=O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([Cl:14])=[O:6]

Participants

4

Reactant 2

HCID 113702-Methoxybenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 889692-Methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 2-methoxybenzoic acid (45.6 g, 0.3 mol), thionyl chloride (53.5 g, 33 ml, 0.45 mol) and dimethylformamide (two drops) was refluxed for an hour. Excess thionyl chloride was then distilled off under reduced pressure. Benzene (50 ml) was added to the residue and the solvent was distilled off until the weight of the residue remained unchanged (about 51 g).

Workup

  1. temperaturewas refluxed for an hour
  2. distillationExcess thionyl chloride was then distilled off under reduced pressure
  3. additionBenzene (50 ml) was added to the residue
  4. distillationthe solvent was distilled off until the weight of the residue

Sources & evidence

ORD record
ord-0526a816567b44e8b3f8de0f36015387
Source dataset
uspto-grants-2003_08
Patent number
US06610738B2

Reaction notes

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