Nitric Acid → 5-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzaldehyde

HRID 1902995Notes

Reaction equation

HRID 1902995 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[C:9]([CH:12]=1)[CH2:10][OH:11].[N+]([O-])(O)=O>[N+](C)([O-])=O.O>[Cl:1][C:2]1[CH:19]=[C:18]([C:20]([F:21])([F:23])[F:22])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[C:9]([CH:12]=1)[CH:10]=[O:11]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 13050461HCID 13050461, compound

Product 1

HCID 130569775-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzaldehydeYield 50.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6375NitromethaneSolvent

Procedure

100 g of 5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitrobenzyl alcohol were dissolved in 370 ml of nitromethane. A mixture of 86.4 g of 65% strength nitric acid and 43.2 g of water was then added dropwise in the course of 90 minutes to this solution, at 60° to 65° C., and the mixture was stirred for 8 hours at 60° to 65° C. It was then diluted with 4 liters of water, and the product was filtered off. 50.2 g (50% of theory) of 5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzaldehyde, of melting point 95° C., were obtained.

Workup

  1. additionwas then added dropwise in the course of 90 minutes to this solution, at 60° to 65° C.
  2. filtrationthe product was filtered off

Sources & evidence

ORD record
ord-5fbc703281d140eeb8e7b588ac85cfcd
Source dataset
uspto-grants-1984_03
Patent number
US04435208

Reaction notes

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