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

HRID 2244292Notes

Reaction equation

HRID 2244292 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

Conditions

Temperature
45 °C

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 began immediately. After 30 minutes the reaction mixture was warmed in a 45° C. 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 again evaporated in vacuo. Finally, dry toluene was added to the residue and this was evaporated at reduced pressure. The crude acid chloride was used without further purification in the following step.

Workup

  1. customBubbling
  2. temperatureThe solution was cooled to room temperature
  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 again evaporated in vacuo
  7. additionFinally, dry toluene was added to the residue
  8. customthis was evaporated at reduced pressure
  9. customThe crude acid chloride was used without further purification in the following step

Sources & evidence

ORD record
ord-9285cac1acaa4d6eaa2c3d5db4a543d2
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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