Thionyl Chloride → Chlorocarbonyl methoxy-acetic acid benzyl ester

HRID 1398106Notes

Reaction equation

HRID 1398106 reaction equation
[CH2:1]([O:8][C:9]([CH:11]([O:15][CH3:16])[C:12](O)=[O:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O>>[CH2:1]([O:8][C:9](=[O:10])[CH:11]([C:12]([Cl:19])=[O:13])[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 68162375Benzyloxycarbonyl methoxy-acetic acid

Product 1

HCID 86669389Chlorocarbonyl methoxy-acetic acid benzyl ester

Procedure

A solution of Benzyloxycarbonyl methoxy-acetic acid (40 g) and Thionyl Chloride (80 ml) was stirred at reflux temperature for 3 hours. Excess Thionyl Chloride was distilled off and to the residue was added Toluene (100 ml). The solvent was distilled off completely to get chlorocarbonyl methoxy-acetic acid benzyl ester (40 g) as a light brown liquid which was used without further purification.

Workup

  1. temperatureat reflux temperature for 3 hours
  2. distillationExcess Thionyl Chloride was distilled off and to the residue
  3. additionwas added Toluene (100 ml)
  4. distillationThe solvent was distilled off completely

Sources & evidence

ORD record
ord-10a0e3dc39fc4f68969306e624956ca5
Source dataset
uspto-grants-2014_12
Patent number
US08901341B2

Reaction notes

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