Toluene → HCID 2387345, compound

HRID 1105714Notes

Reaction equation

HRID 1105714 reaction equation
[OH-].[K+].C1(C)C=CC=CC=1.[Cl:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:12]=1[C:13]([OH:15])=[O:14].Cl[CH2:22][C:23]([NH2:25])=[O:24]>C(OCC)(=O)C.O>[Cl:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:12]=1[C:13]([O:15][CH2:22][C:23]([NH2:25])=[O:24])=[O:14]

Participants

7

Reactant 4

HCID 1140TolueneHCID 57582,6-Dichlorobenzoic acidHCID 6580ChloroacetamideHCID 14797Potassium Hydroxide

Product 1

HCID 2387345HCID 2387345, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A sample of 5.9 grams (0.105 mole) of potassium hydroxide was ground to a powder and placed in the reaction vessel. To this was added 270 ml of dry toluene, followed by 20.0 grams (0.105 mole) of 2,6-dichlorobenzoic acid. The stirred reaction mixture was heated under reflux while the water by-product was collected by azeotropic distillation using a Dean-Stark trap. A total of 2.8 ml of water was collected during a 30-minute period. At the end of this time the reaction mixture was cooled slightly and 2.0 grams of 1,4,7,10,13,16-hexaoxacyclooctadecane, followed by 9.8 grams (0.105 mole) of chloroacetamide were added. Upon completion of the addition the reaction mixture was heated under reflux for 18 hours. the reaction mixture was cooled to ambient temperature and the toluene layer was separated from the two-phase system and washed with one portion of 100 ml of water. An emulsion formed but was broken up by the addition of 100 ml of ethyl acetate. The organic layer was separated and dried with sodium sulfate. The mixture was filtered, and the filtrate evaporated under reduced pressure to a residual semi-solid. The solid was recrystallized twice from high-boiling petroleum ether-ethyl acetate using decolorizing carbon to give 12.6 grams of (aminocarbonyl)methyl 2,6-dichlorobenzoate; mp 113.5°-115.5°. The ir and the nmr spectra were consistent with the proposed structure.

Workup

  1. customThe stirred reaction mixture
  2. temperaturewas heated
  3. distillationwas collected by azeotropic distillation
  4. customA total of 2.8 ml of water was collected during a 30-minute period
  5. temperatureAt the end of this time the reaction mixture was cooled slightly
  6. additionwere added
  7. additionUpon completion of the addition the reaction mixture
  8. temperaturewas heated
  9. temperatureunder reflux for 18 hours
  10. customthe toluene layer was separated from the two-phase system
  11. washwashed with one portion of 100 ml of water
  12. customAn emulsion formed
  13. customThe organic layer was separated
  14. dry with materialdried with sodium sulfate
  15. filtrationThe mixture was filtered
  16. customthe filtrate evaporated under reduced pressure to a residual semi-solid
  17. customThe solid was recrystallized twice from high-boiling petroleum ether-ethyl acetate using

Sources & evidence

ORD record
ord-2721be061fa04511b5ed8191af544fe0
Source dataset
uspto-grants-1982_01
Patent number
US04309566

Reaction notes

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