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

HRID 1855702Notes

Reaction equation

HRID 1855702 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-b12259e8c372437c99957bc9d712d514
Source dataset
uspto-grants-1980_08
Patent number
US04216152

Reaction notes

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