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

HRID 1479690Notes

Reaction equation

HRID 1479690 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 49.9%HCID 74404-Nitro-o-xylene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

The 250 mL three-necked round bottom flask fitted with reverse dean-stark apparatus was charged with 21.215 g o-xylene (0.2 mol), 120 mL 1,2 dichloro ethane, and 4.242 g of catalyst as prepared in example 6. The flask was flushed with nitrogen. The reaction mixture was refluxed at 110° C. for 1 h followed by the dropwise addition of 35.6 mL (0.266 mol) 70% HNO3. The water formed during the reaction was removed using reverse dean-stark apparatus. The reaction was carried out for 8 h. The reaction was monitored by GC analysis. In this reaction 48.2% conversion of o-xylene was obtained with 49.7% and 49.9% 3-nitro o-xylene (3NOx) and 4-nitro o-xylene (4NOx), respectively. Other unidentified products were 0.4%.

Workup

  1. customThe 250 mL three-necked round bottom flask fitted with reverse dean-stark apparatus
  2. customas prepared in example 6
  3. customThe flask was flushed with nitrogen
  4. customwas removed
  5. customIn this reaction 48.2% conversion of o-xylene

Sources & evidence

ORD record
ord-8d92bdf543b94da38c5192204d94f46a
Source dataset
uspto-grants-2016_08
Patent number
US09409854B2

Reaction notes

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