1,2-Dichloroethane → 2-Nitrotoluene

HRID 1479694Notes

Reaction equation

HRID 1479694 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClCCCl.[N+:12]([O-:15])([OH:14])=[O:13]>O>[N+:12]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:7])([O-:14])=[O:13].[N+:12]([C:4]1[CH:5]=[CH:6][C:1]([CH3:7])=[CH:2][CH:3]=1)([O-:15])=[O:13]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 944Nitric AcidHCID 1140Toluene

Product 2

HCID 69442-NitrotolueneHCID 74734-Nitrotoluene

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 9.214 g toluene (0.1 mol), 40 mL 1,2 dichloro ethane, and 1.842 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 8.6 mL (0.133 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 80.5% toluene conversion was obtained with 54.7% selectivity for 2-nitro toluene and 41.6% for 4-nitro toluene. Other products were 3.7%.

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 80.5% toluene conversion

Sources & evidence

ORD record
ord-307a4a1eac894ba787de1301e56da65e
Source dataset
uspto-grants-2016_08
Patent number
US09409854B2

Reaction notes

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