Hydrochloric Acid → 3,5-Diethylnitrobenzene

HRID 1657930Notes

Reaction equation

HRID 1657930 reaction equation
[CH2:1]([C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([CH2:13][CH3:14])[C:4]=1N)[CH3:2].Cl.N([O-])=O.[Na+].[PH2](O)=O>O>[CH2:1]([C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([CH2:13][CH3:14])[CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4124402Phosphinic AcidHCID 81426772,6-Diethyl-4-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 145959433,5-Diethylnitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 19.4 parts of 2,6-diethyl-4-nitroaniline in 40 parts by volume of concentrated hydrochloric acid is diluted with 80 parts of water and added to 100 parts of ice. A solution of 7 parts of sodium nitrite in 15 parts of water is added and the filtered diazonium solution treated with 150 parts by volume of 50% hypophosphorous acid and kept cold for 24 hours. The 3,5-diethylnitrobenzene which separates is extracted with ether and distilled, b.p. 190°/20mm.

Workup

  1. additionadded to 100 parts of ice
  2. extractionThe 3,5-diethylnitrobenzene which separates is extracted with ether
  3. distillationdistilled

Sources & evidence

ORD record
ord-82c96d0ba24a455aa09566e9fa7c33d1
Source dataset
uspto-grants-1976_06
Patent number
US03962307

Reaction notes

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