Oxalyl chloride → 4-Chloro-o-tolyloxyacetic acid chloride

HRID 639277Notes

Reaction equation

HRID 639277 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([O:9][CH2:10][C:11]([OH:13])=O)[CH:3]=1.C(Cl)(=O)C([Cl:17])=O>ClCCl.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([O:9][CH2:10][C:11]([Cl:17])=[O:13])[CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 164957292-(5-Chloro-2-methylphenoxy)acetic acid

Product 1

HCID 1298977964-Chloro-o-tolyloxyacetic acid chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a cold suspension of 4-chloro-o-tolyloxyacetic acid (17.4 mmol) in 40 mL of dry dichloromethane was added oxalyl chloride (39.15 mmol) followed by one drop of N,N-dimethylformamide. Bubbling immediately began. After 30 minutes, the reaction mixture was warmed in a 45° oil bath for 1.5 hours. The solution was cooled to room temperature and all volatiles were removed by evaporation. Dry nitrogen gas was introduced into the evaporator and more dry dichloromethane was added. This was evaporated again in vacuo. Finally, dry toluene was added to the residue and this was evaporated at reduced pressure. The prepared acid chloride was used without further purification in the following step.

Workup

  1. customBubbling immediately
  2. temperaturethe reaction mixture was warmed in a 45° oil bath for 1.5 hours
  3. customall volatiles were removed by evaporation
  4. additionDry nitrogen gas was introduced into the evaporator and more dry dichloromethane
  5. additionwas added
  6. customThis was evaporated again in vacuo
  7. additionFinally, dry toluene was added to the residue
  8. customthis was evaporated at reduced pressure
  9. customThe prepared acid chloride was used without further purification in the following step

Sources & evidence

ORD record
ord-594526c534df4505af199cd70ad81f75
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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