2,5-Dichloronitrobenzene → 2-(4-Chloro-2-nitrophenoxy)benzaldehyde

HRID 2399369Notes

Reaction equation

HRID 2399369 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[K].[CH:13](=[O:21])[C:14]1[C:15](=[CH:17][CH:18]=[CH:19][CH:20]=1)[OH:16]>O>[N+:9]([C:3]1[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=1[O:16][C:15]1[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=1[CH:13]=[O:21])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 69772,5-DichloronitrobenzeneHCID 6998SalicylaldehydeHCID 5462222Potassium

Product 1

HCID 157803122-(4-Chloro-2-nitrophenoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Briefly, 200 parts of 2,5-dichloro-nitrobenzene were heated to 160° C. and stirred, and 160 parts of the potassium salt of salicylaldehyde was added over a period of 30 minutes. After the addition was complete, an exothermic reaction took place, and the temperature rose to about 195° C. Heating was discontinued until the reaction subsided, and the mixture was heated for 1 hour. at 150° C. The mixture was cooled, ice and water were added, and it was extracted with ether. The ether layer was filtered to remove insoluble material, and the resultant solution was dried over sodium sulfate. The ether solvent was evaporated, and the residual oil was recrystallized from a mixture of hexane and benzene to give 2-(2-nitro-4-chloro-phenoxy)benzaldehyde melting at about 100°-101° C.

Workup

  1. additionAfter the addition
  2. customan exothermic reaction
  3. customrose to about 195° C
  4. temperatureHeating
  5. temperaturethe mixture was heated for 1 hour
  6. customat 150° C
  7. temperatureThe mixture was cooled
  8. extractionit was extracted with ether
  9. filtrationThe ether layer was filtered
  10. customto remove insoluble material
  11. dry with materialthe resultant solution was dried over sodium sulfate
  12. customThe ether solvent was evaporated
  13. customthe residual oil was recrystallized from a mixture of hexane and benzene

Sources & evidence

ORD record
ord-c166afd91ac0421585d16ded13962f1a
Source dataset
uspto-grants-1995_09
Patent number
US05449673

Reaction notes

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