1,2-Dichloroethane → 1,2-Dimethyl-3-nitrobenzene

HRID 1479688Notes

Reaction equation

HRID 1479688 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=1[CH3:8].ClCCCl.[N+:13]([O-:16])([OH:15])=[O:14]>O>[N+:13]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[CH3:1])([O-:15])=[O:14].[N+:13]([C:4]1[CH:3]=[C:2]([CH3:1])[C:7]([CH3:8])=[CH:6][CH:5]=1)([O-:16])=[O:14]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 944Nitric AcidHCID 7237O-Xylene

Product 2

HCID 67391,2-Dimethyl-3-nitrobenzeneYield 51.1%HCID 74404-Nitro-o-xylene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A 250 mL three-necked round bottom flask fitted with reverse dean-stark apparatus was charged with 10.62 g o-xylene (0.1 mol), 60 mL 1,2 dichloro ethane, and 2.12 g of catalyst as prepared in example 5. The reaction flask was flushed with nitrogen. The reaction mixture was refluxed at 110° C. for 1 h followed by the dropwise addition of 11.35 mL (0.2 mol) 70% HNO3. The water formed during the reaction was removed using the reverse dean-stark apparatus. The reaction was carried out for 16 h. The reaction was monitored by GC analysis. In this reaction 94.9% conversion of o-xylene was obtained with 48.0% and 51.1% 3-nitro o-xylene (3NOx) and 4-nitro o-xylene (4NOx), respectively. Other unidentified products were 0.9%.

Workup

  1. customA 250 mL three-necked round bottom flask fitted with reverse dean-stark apparatus
  2. customas prepared in example 5
  3. customThe reaction flask was flushed with nitrogen
  4. customwas removed
  5. customIn this reaction 94.9% conversion of o-xylene

Sources & evidence

ORD record
ord-d63f4821bfde4c35a0a921fbfec00c15
Source dataset
uspto-grants-2016_08
Patent number
US09409854B2

Reaction notes

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