Toluene → 4-Formylbenzoyl chloride

HRID 482816Notes

Reaction equation

HRID 482816 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 Chloride

Product 1

HCID 124246204-Formylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The title substance was synthesized as follows: 300 ml of thionyl chloride was dropped into a mixture of 358 g of commercially available terephthalaldehydic acid with 700 ml of toluene and 2 g of pyridine, and the solution was heated under reflux slowly until a homogeneous reaction solution was obtained. After the solution was cooled to room temperature, unreacted thionyl chloride and toluene as a solvent were distilled off in vacuum. Terephthalaldehydic acid chloride (b.p. 133°-135° C./15 Torr) was obtained by the vacuum distillation of the remaining reaction product.

Workup

  1. customThe title substance was synthesized
  2. temperaturethe solution was heated
  3. temperatureunder reflux slowly until a homogeneous reaction solution
  4. customwas obtained
  5. distillationunreacted thionyl chloride and toluene as a solvent were distilled off in vacuum

Sources & evidence

ORD record
ord-5a064abc5ffa42899e5dd959a8912764
Source dataset
uspto-grants-1986_03
Patent number
US04576732

Reaction notes

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