1,2-Dichloroethane → Nitrobenzene

HRID 1479693Notes

Reaction equation

HRID 1479693 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClCCCl.[N+:11]([O-])([OH:13])=[O:12]>O>[N+:11]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 241BenzeneHCID 944Nitric Acid

Product 1

HCID 7416Nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 100 mL three-necked reaction flask fitted with reverse dean-stark apparatus was charged with 7.8 g benzene (0.1 mol), 60 mL 1,2 dichloro ethane, and 1.56 g of catalyst as prepared in example 5. The flask was flushed with nitrogen. The reaction mixture was refluxed at 100° C. for 1 h followed by dropwise addition of 6.42 mL (0.1 mol) of 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 18.6% benzene conversion was obtained with 100% selectivity for mono nitro benzene.

Workup

  1. customA 100 mL three-necked reaction flask fitted with reverse dean-stark apparatus
  2. customas prepared in example 5
  3. customThe flask was flushed with nitrogen
  4. customwas removed
  5. customIn this reaction 18.6% benzene conversion

Sources & evidence

ORD record
ord-decd51250ee940139b25270c0f81a909
Source dataset
uspto-grants-2016_08
Patent number
US09409854B2

Reaction notes

Loading…