4-Nitrophenol → 1-(2-Chloroethoxy)-4-nitrobenzene

HRID 329376Notes

Reaction equation

HRID 329376 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(S(O[CH2:21][CH2:22][Cl:23])(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:21][CH2:22][Cl:23])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 136344852-Chloroethyl Benzenesulfonate

Product 1

HCID 27645871-(2-Chloroethoxy)-4-nitrobenzeneYield 82.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-nitrophenol (139 g, 1 mole), 2-(benzenesulphonyloxy)ethyl chloride (220.5 g, 1 mole--see Ber. (1920), 53, 1836) and anhydrous potassium carbonate (138 g, 1 mole) in methyl ethyl ketone ("MEK"--1000 ml) was stirred at reflux for 16 hours. After cooling, the mixture was poured onto water and the organic layer was separated. Following two further extractions with methyl ethyl ketone, the combined organic fractions were dried (MgSO4), filtered and evaporated. The resultant solid was crystallised from ethanol to give the title compound, (165.8 g), m.p. 60°.

Workup

  1. temperatureat reflux for 16 hours
  2. temperatureAfter cooling
  3. additionthe mixture was poured onto water
  4. customthe organic layer was separated
  5. extractiontwo further extractions with methyl ethyl ketone
  6. dry with materialthe combined organic fractions were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe resultant solid was crystallised from ethanol

Sources & evidence

ORD record
ord-715e837dbe5b4fa0b4e65e2d8ac2acac
Source dataset
uspto-grants-1990_01
Patent number
US04891372

Reaction notes

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