4-Nitrophenol → 1-(3-Chloropropoxy)-4-nitrobenzene

HRID 1709821Notes

Reaction equation

HRID 1709821 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:12][CH2:13][CH2:14][Cl:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:15][CH2:14][CH2:13][CH2:12][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 118446171-(3-Chloropropoxy)-4-nitrobenzeneYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7.0 g (0.05 mole) of 4-nitrophenol, 15.7 g (0.1 mole) of 1-bromo-3-chloropropane and 20.7 g (0.15 mole) of anhydrous potassium carbonate in 350 ml of acetone was heated at reflux for 17 hr. The mixture was cooled, filtered, and the filtrate was concentrated to give an oil which crystallized. The solid was collected by filtration, washed with petroleum ether, and dried to yield 10.1 g (94%) of the title compound. An analytical sample was prepared from ethyl ether-petroleum ether, m.p. 37°-39° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 17 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customto give an oil which
  7. customcrystallized
  8. filtrationThe solid was collected by filtration
  9. washwashed with petroleum ether
  10. customdried

Sources & evidence

ORD record
ord-0ddcfcff746e479e98130ac81feb0c0e
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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