Chloroacetic Acid → Phenoxyacetic Acid

HRID 1265997Notes

Reaction equation

HRID 1265997 reaction equation
[OH-:1].[K+].Cl[CH2:4][C:5]([OH:7])=[O:6].[C:8]1(C)[C:9](C)=[CH:10][CH:11]=[CH:12][CH:13]=1>>[O:1]([CH2:4][C:5]([OH:7])=[O:6])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 300Chloroacetic AcidHCID 7237O-XyleneHCID 14797Potassium Hydroxide

Product 1

HCID 19188Phenoxyacetic Acid

Procedure

300 g of technical cashew nut shell liquid and 500 ml of xylene was charged to a 2 liter reactor equipped with agitator and condenser. The contents were warmed to 40 degree C. Subsequently 168 g of potassium hydroxide was added to the reactor and stirred for 40 minutes. Later, 94 g of chloro acetic acid was added slowly in 30 minutes. After the completion of addition of reactants, the reaction mixture was refluxed for 6 hours. On completion of the reaction, the solvent was removed and contents taken in water and acidified with dilute sulfuric acid. The mixture was extracted with hexane to yield semi solid CNSL phenoxy acetic acid.

Workup

  1. customequipped with agitator and condenser
  2. temperatureThe contents were warmed to 40 degree C
  3. additionAfter the completion of addition of reactants
  4. temperaturethe reaction mixture was refluxed for 6 hours
  5. customOn completion of the reaction
  6. customthe solvent was removed
  7. extractionThe mixture was extracted with hexane

Sources & evidence

ORD record
ord-b9348330ed734b0fafaa2a25a814af60
Source dataset
uspto-grants-2003_04
Patent number
US06548459B2

Reaction notes

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