Water → 1-(2-chloroethoxy)-2-nitrobenzene

HRID 1852364Notes

Reaction equation

HRID 1852364 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[Cl:11][CH2:12][CH2:13]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:11][CH2:12][CH2:13][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 69472-NitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 43624871-(2-chloroethoxy)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

2-Nitro-phenol (168.7 g) and toluene-4-sulfonic acid 2-chloroethyl ester (100 g) were dissolved in 500 ml DMF and were stirred for 1 h at 110-120° C. after careful addition of 199 g potassium carbonate. The reaction mixture was poured in a mixture of crushed ice and water (8 L) which was vigorously stirred. The residue was filtered off, washed several times with water and dried. Yield: 100-120 g.

Workup

  1. stirringwas vigorously stirred
  2. filtrationThe residue was filtered off
  3. washwashed several times with water
  4. customdried

Sources & evidence

ORD record
ord-aaa3f2253eee4557a9cc2742595f9d62
Source dataset
uspto-grants-2015_02
Patent number
US08962338B2

Reaction notes

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