2,5-Dichloronitrobenzene → 2-(4-Chloro-2-nitrophenoxy)benzaldehyde
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
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
- additionAfter the addition
- customan exothermic reaction
- customrose to about 195° C
- temperatureHeating
- temperatureThe mixture was cooled
- extractionit was extracted with ether
- filtrationThe ether layer was filtered
- customto remove insoluble material
- dry with materialthe resultant solution was dried over sodium sulfate
- customThe ether solvent was evaporated
- customthe residual oil was recrystallized from a mixture of hexane and benzene
Sources & evidence
- ORD record
- ord-09eaa34d8f674c0b9ea956d854c56c14
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05719140
Reaction notes
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