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

HRID 1479687Notes

Reaction equation

HRID 1479687 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 53.7%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 21.205 g o-xylene (0.2 mol), 120 mL 1,2 dichloro ethane, and 4.242 g catalyst as prepared in example 5. The flask was flushed with nitrogen. The solution was refluxed at 110° C. for 1 h. Then 16.4 mL of 70% HNO3 (0.266 mol) was added to the reaction flask dropwise. The water formed during the reaction was removed azeotropically using the reverse dean-stark apparatus. The reaction was carried out for 8 h. The reaction was monitored by GC analysis. In this reaction 74.5% conversion of o-xylene was obtained with 44.8% and 53.7% 3-nitro o-xylene (3NOx) and 4-nitro o-xylene (4NOx), respectively. Other unidentified products were 1.5%.

Workup

  1. customA 250 mL three-necked round bottom flask fitted with reverse dean-stark apparatus
  2. customas prepared in example 5
  3. customThe flask was flushed with nitrogen
  4. customwas removed azeotropically
  5. customIn this reaction 74.5% conversion of o-xylene

Sources & evidence

ORD record
ord-0d75e350b035496b9acd522b951cb9dc
Source dataset
uspto-grants-2016_08
Patent number
US09409854B2

Reaction notes

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