Salicylaldehyde → HCID 802757, compound

HRID 1974539Notes

Reaction equation

HRID 1974539 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 is heated to 160° C. and stirred and 160 parts of the potassium salt of salicylaldehyde is added over a period of 30 minutes. After the addition is complete, an exothermic reaction takes place and the temperature rises to about 195° C. Heating is then discontinued until the reaction subsides and the mixture is then heated for 1 hour at 150° C. The mixture is cooled, ice and water are added, and it is then extracted with ether. The ether layer is filtered to remove insoluble material and the resultant solution is dried over sodium sulfate. The ether solvent is then evaporated and the residual oil is recrystallized from a mixture of hexane and benzene to give 2-(2-nitro-4-trifluoromethyl-phenoxy)benzaldehyde melting at about 79°-81° C.

Workup

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

Sources & evidence

ORD record
ord-c34fc8ae02de49e990cab04fc61b7295
Source dataset
uspto-grants-1994_02
Patent number
US05283240

Reaction notes

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