Thionyl Chloride → Methyl 4-(chlorocarbonyl)benzoate

HRID 1110160Notes

Reaction equation

HRID 1110160 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-])=[O:7])=[CH:4][CH:3]=1.S(Cl)([Cl:16])=O>O>[C:1]([C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:16])=[O:7])=[CH:4][CH:3]=1)([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 36144541,4-Benzenedicarboxylic acid, methyl ester

Product 1

HCID 81850Methyl 4-(chlorocarbonyl)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Monomethyl terephthalate (10.2 g, 0.057 mol) and thionylchloride (50 ml) were mixed in a 100 ml three-necked flask and stirred under gentle reflux overnight. The cooling water was shut off and excess thionylchloride swept away in a stream of nitrogen. By raising the temperature, the product then was distilled and collected as white crystals of high purity.

Workup

  1. temperatureunder gentle reflux overnight
  2. temperatureBy raising the temperature
  3. distillationthe product then was distilled
  4. customcollected as white crystals of high purity

Sources & evidence

ORD record
ord-53bfe46f4fb04b939db33f5876a465eb
Source dataset
uspto-grants-1994_06
Patent number
US05324859

Reaction notes

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