Toluene → Phenoxyacetic Acid

HRID 1265999Notes

Reaction equation

HRID 1265999 reaction equation
[OH-:1].[K+].ClCC([O:7][C:8](=[O:11])[CH2:9]Cl)=O.[C:12]1(C)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[O:1]([CH2:9][C:8]([OH:7])=[O:11])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 10946Chloroacetic anhydrideHCID 14797Potassium Hydroxide

Product 1

HCID 19188Phenoxyacetic Acid

Procedure

304 g of alkyl phenol derived by partial hydrogenation of distilled cashew nut shell liquid and 650 ml of toluene was charged to a 2 liter reactor equipped with agitator and condenser. The contents were warmed to 40 degree C. Subsequently 112 g of potassium hydroxide was added to the reactor and stirred for 40 minutes. Later, 85 g of chloro acetic anhydride 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 product got separated from the aqueous mixture, which was filtered and recrystallised from methanol.

Workup

  1. additionwas charged to a 2 liter reactor
  2. customequipped with agitator and condenser
  3. temperatureThe contents were warmed to 40 degree C
  4. additionAfter the completion of addition of reactants
  5. temperaturethe reaction mixture was refluxed for 6 hours
  6. customOn completion of the reaction
  7. customthe solvent was removed
  8. customThe product got separated from the aqueous mixture, which
  9. filtrationwas filtered
  10. customrecrystallised from methanol

Sources & evidence

ORD record
ord-e3204d336a18454c8594cfac8e434116
Source dataset
uspto-grants-2003_04
Patent number
US06548459B2

Reaction notes

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