1,2-Dichloroethane → 4-Methyl-2-nitrophenol

HRID 1479697Notes

Reaction equation

HRID 1479697 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.ClCCCl.[N+:13]([O-])([OH:15])=[O:14]>O>[N+:13]([C:5]1[C:6]([OH:7])=[CH:1][CH:2]=[C:3]([CH3:8])[CH:4]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 944Nitric AcidHCID 2879P-Cresol

Product 1

HCID 83914-Methyl-2-nitrophenolYield 99.1%

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 10.804 g (0.1 mol) p-cresol, 65 mL 1,2 dichloro ethane, and 2.161 g of catalyst as prepared in example 5. The flask was flushed with nitrogen. The reaction mixture was refluxed at 110° C. for 1 h followed by dropwise addition of 8.6 mL (0.133 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, 98.7% conversion of p-cresol was obtained with 99.1% 2-nitro p-cresol and 0.9% of other products.

Workup

  1. customA 100 mL reaction flask
  2. customfitted with reverse dean-stark apparatus
  3. customas prepared in example 5
  4. customThe flask was flushed with nitrogen
  5. customwas removed
  6. customIn this reaction, 98.7% conversion of p-cresol

Sources & evidence

ORD record
ord-0f294b4987cc415895cbfbc37fb15d42
Source dataset
uspto-grants-2016_08
Patent number
US09409854B2

Reaction notes

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