1,2-Dichloroethane → Phenol

HRID 1479696Notes

Reaction equation

HRID 1479696 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClCCCl.[N+:12]([O-:15])([OH:14])=[O:13]>O>[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:12]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[OH:7])([O-:14])=[O:13].[N+:12]([C:4]1[CH:5]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=1)([O-:15])=[O:13]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 944Nitric AcidHCID 996Phenol

Product 3

HCID 9804-NitrophenolYield 46.5%HCID 996PhenolYield 100%HCID 69472-NitrophenolYield 46.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A 100 mL three-necked round bottom flask fitted with reverse dean-stark apparatus was charged with 9.411 g (0.1 mol) phenol, 60 mL 1,2 dichloro ethane and 1.882 g of catalyst as prepared in example 5. The reaction 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) 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 case, 100% phenol conversion was obtained with 46.5% 2-nitro phenol and 46.5% 4-nitro phenol. Other unidentified products were 7%.

Workup

  1. customA 100 mL three-necked round bottom flask fitted with reverse dean-stark apparatus
  2. customas prepared in example 5
  3. customThe reaction flask was flushed with nitrogen
  4. customwas removed

Sources & evidence

ORD record
ord-44873f563b9b4e38836fe210ed944f9f
Source dataset
uspto-grants-2016_08
Patent number
US09409854B2

Reaction notes

Loading…