Toluene → 4-Formylbenzoyl chloride

HRID 648872Notes

Reaction equation

HRID 648872 reaction equation
S(Cl)([Cl:3])=O.[C:5]([OH:15])(=O)[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.C1(C)C=CC=CC=1>N1C=CC=CC=1>[C:5]([Cl:3])(=[O:15])[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 120884-Formylbenzoic acidHCID 24386Thionyl Chloride2×

Product 1

HCID 124246204-Formylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Thionyl chloride (300 ml) was added to a mixed solution of commercially available terephthalaldehydic acid (350 g), toluene (700 ml) and pyridine (2 ml), followed by stirring at room temperature, thereafter heating the mixture on a water bath at 60° C. with stirring, further heating to 110° C. on a mantle heater, cautiously adding thionyl chloride (100 ml), heating at 150° C. for 3 hours with stirring, distilling off excess thionyl chloride under reduced pressure and distilling the residue under reduced pressure to obtain terephthalaldehydic acid chloride (328 g) (b.p. 133°~134° C./14 mmHg).

Workup

  1. temperatureheating the mixture on a water bath at 60° C.
  2. stirringwith stirring
  3. temperatureheating at 150° C. for 3 hours
  4. stirringwith stirring
  5. distillationdistilling off excess thionyl chloride under reduced pressure
  6. distillationdistilling the residue under reduced pressure

Sources & evidence

ORD record
ord-5e59aa3646b54780a7abd40fc102508f
Source dataset
uspto-grants-1988_04
Patent number
US04737313

Reaction notes

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