Hydrochloric Acid → HCID 14012549, compound

HRID 652839Notes

Reaction equation

HRID 652839 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9].[Cl:15][C:16]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:17]=1[O:18][CH2:19][C:20]([OH:22])=[O:21].Cl>C(=S)=S>[Cl:15][C:16]1[C:26]([Cl:27])=[C:25]([C:8](=[O:9])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[F:5])[CH:24]=[CH:23][C:17]=1[O:18][CH2:19][C:20]([OH:22])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 98082-Fluorobenzoyl chlorideHCID 181052,3-Dichlorophenoxyacetic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14012549HCID 14012549, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a mixture of 12.5 g of aluminum chloride and 45 ml of carbon disulfide there is added dropwise 7.1 g of 2-fluorobenzoyl chloride while maintaining the temperature below 0° C. This low temperature is maintained for 1.5 hours. While maintaining this same low temperature, 5 g of 2,3-dichlorophenoxyacetic acid is added incrementally. After addition is complete, the reaction mixture is maintained at low temperature for 30 minutes and then permitted to reach ambient temperature after which it is refluxed for 28 hours. The carbon disulfide is decanted from the refluxed solution leaving a dark orange residue which is poured onto a mixture of 500 ml of ice/water and 100 ml of concentrated hydrochloric acid. The resulting pink precipitate is collected by filtration, rinsed with 300 ml of warm water (50° C.) and dried in vacuum oven. The dried product is recrystallized twice from aqueous ethyl alcohol to form the product 2,3-dichloro-4-(2-fluorobenzoyl)phenoxyacetic acid having a melting point of 153° to 156° C.

Workup

  1. temperaturewhile maintaining the temperature below 0° C
  2. temperatureThis low temperature is maintained for 1.5 hours
  3. additionis added incrementally
  4. additionAfter addition
  5. temperaturethe reaction mixture is maintained at low temperature for 30 minutes
  6. customto reach ambient temperature
  7. temperatureis refluxed for 28 hours
  8. customThe carbon disulfide is decanted from the refluxed solution
  9. customleaving a dark orange residue which
  10. filtrationThe resulting pink precipitate is collected by filtration
  11. washrinsed with 300 ml of warm water (50° C.)
  12. customdried in vacuum oven
  13. customThe dried product is recrystallized twice from aqueous ethyl alcohol

Sources & evidence

ORD record
ord-12f64e3b9fa64d7fb0dc3a36dfd77bc7
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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