Salicylaldehyde → HCID 802757, compound

HRID 1464447Notes

Reaction equation

HRID 1464447 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[K].[CH:16](=[O:24])[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[OH:19]>O>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[O:19][C:18]1[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=1[CH:16]=[O:24])([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 5462222Potassium

Product 1

HCID 802757HCID 802757, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

200 parts of 4-chloro-3-nitrobenzotrifluoride was 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 then discontinued until the reaction subsided, and the mixture was then heated for 1 hour at 150° C. The mixture was cooled, ice and water were added, and it was then 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 then evaporated and the residual oil was recrystallized from a mixture of hexane and benzene to give 2-(2-nitro-4-trifluoromethylphenoxy)benzaldehyde melting at about 79°-81° C.

Workup

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

Sources & evidence

ORD record
ord-e4f0779e449247e4895a495370f48f72
Source dataset
uspto-grants-1994_04
Patent number
US05304644

Reaction notes

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