4-Formylbenzoic acid → 4-Formylbenzoyl chloride

HRID 1109951Notes

Reaction equation

HRID 1109951 reaction equation
[C:1]([OH:11])(=O)[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.S(Cl)([Cl:14])=O>N1C=CC=CC=1>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([C:1]([Cl:14])=[O:11])=[CH:3][CH:4]=1)=[O:7]

Participants

4

Reactant 2

HCID 120884-Formylbenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 124246204-Formylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 7.50 g of terephthalaldehydic acid (4-formylheuzoic acid) were added 20 ml of thionyl chloride and 1 ml of pyridine, followed by heating under stirring. After the reaction mixture became clear, stirring was further continued at reflux for 4 hours, followed by allowing to cool. The excess thionyl chloride was removed by distillation under reduced pressure, toluene was added to the residue, and any insoluble matter was separated by filtration. The toluene was removed from the filtrate by distillation to obtain 7.91 g of 4-formylbenzoyl chloride.

Workup

  1. temperatureby heating
  2. stirringstirring
  3. temperatureat reflux for 4 hours
  4. temperatureto cool
  5. customThe excess thionyl chloride was removed by distillation under reduced pressure, toluene
  6. additionwas added to the residue
  7. customany insoluble matter was separated by filtration
  8. customThe toluene was removed from the filtrate by distillation

Sources & evidence

ORD record
ord-56db29505db3498586ada525200bf57d
Source dataset
uspto-grants-1994_06
Patent number
US05324451

Reaction notes

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