1,2-Dichloroethane → 1-Chloro-2-nitrobenzene

HRID 1479695Notes

Reaction equation

HRID 1479695 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCCl.[N+:12]([O-:15])([OH:14])=[O:13]>O>[N+:12]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])([O-:14])=[O:13].[N+:12]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)([O-:15])=[O:13]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 944Nitric AcidHCID 7964Chlorobenzene

Product 2

HCID 69451-Chloro-2-nitrobenzeneYield 61.8%HCID 74741-Chloro-4-nitrobenzeneYield 38.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A 100 mL reaction flask fitted with reverse dean-stark apparatus was charged with 11.250 g chlorobenzene (0.1 mol), 48 mL 1,2 dichloro ethane and 2.250 g of catalyst as prepared example 5. The flask was flushed with nitrogen. The reaction mixture was refluxed at 110° C. for 1 h followed by the dropwise addition of 8.6 mL (0.133 mol) 70% HNO3. The water formed during the reaction was removed using fitted with reverse dean-stark apparatus. The reaction was carried out for 8 h. The reaction was monitored by GC analysis. In this reaction 55.2% conversion of chlorobenzene was obtained with 61.8% of 2-nitro chlorobenzene and 38.2% of 4-nitro chlorobenzene.

Workup

  1. customA 100 mL reaction flask
  2. customfitted with reverse dean-stark apparatus
  3. customas prepared example 5
  4. customThe flask was flushed with nitrogen
  5. customwas removed
  6. customusing fitted with reverse dean-stark apparatus
  7. customIn this reaction 55.2% conversion of chlorobenzene

Sources & evidence

ORD record
ord-9bebed44a9924e4e8bb69bafc2018259
Source dataset
uspto-grants-2016_08
Patent number
US09409854B2

Reaction notes

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