Thionyl Chloride → Methyl 4-(chlorocarbonyl)benzoate

HRID 1734575Notes

Reaction equation

HRID 1734575 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-c248ff9529e54372a1ade507ce2f67c4
Source dataset
uspto-grants-1996_07
Patent number
US05534531

Reaction notes

Loading…