2-Nitrophenol → 1-(Cyclopentyloxy)-2-nitrobenzene

HRID 1395354Notes

Reaction equation

HRID 1395354 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[CH:11]1(Br)[CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:11]1([O:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 8728BromocyclopentaneHCID 11430Potassium Carbonate

Product 1

HCID 221644731-(Cyclopentyloxy)-2-nitrobenzeneYield 46.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Nitrophenol (83.5 g, 0.60 mole), cyclopentyl bromide (98.0 g, 0.66 mole), anhydrous potassium carbonate (82.9 g, 0.60 mole) and dry acetone (600 cc) were refluxed for 72 hours, and filtered to remove the potassium bromide. The residue was washed with acetone and the solvent was removed by rotary evaporation. The residue was partitioned between 200 cc of dichloromethane and water. The dichloromethane layer was washed with 200 cc of 10% potassium hydroxide, separated and the solvent was removed by rotary evaporation. The crude product was fractionally distilled at 144°-146° C. at 1.0 mm. Hg to yield 58.2 g of product (46.8%).

Workup

  1. filtrationfiltered
  2. customto remove the potassium bromide
  3. washThe residue was washed with acetone
  4. customthe solvent was removed by rotary evaporation
  5. customThe residue was partitioned between 200 cc of dichloromethane and water
  6. washThe dichloromethane layer was washed with 200 cc of 10% potassium hydroxide
  7. customseparated
  8. customthe solvent was removed by rotary evaporation
  9. distillationThe crude product was fractionally distilled at 144°-146° C. at 1.0 mm. Hg

Sources & evidence

ORD record
ord-58a327a77b474e7b9dd77fb50849ffe3
Source dataset
uspto-grants-1980_05
Patent number
US04203901

Reaction notes

Loading…