2-Nitrophenol → 1-Nitro-2-propoxybenzene

HRID 67241

Reaction equation

HRID 67241 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].Br[CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:12]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 78401-BromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 5874971-Nitro-2-propoxybenzeneYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

o-Nitrophenol (111.2 g., 0.8 mole), 1-bromopropane (98.4 g., 0.8 mole), anhydrous potassium carbonate (121.4 g., 0.88 mole) and any acetone (800 cc) are refluxed for 70 hrs., filtered the reaction mass, the residue was washed with acetone, and the filtrate rotoevaporated. To the residue of the evaporation was added 200 cc of dichloromethane and rotoevaporated again; the residue was washed with 100 cc of water and separated into two layers. The dichloromethane layer was washed with 100 cc of 10% Na2CO3, separated again, washed again with 100 cc of water, and the dichloromethane layer was fractionated under vacuum. The main fraction distilled at 103°-106° C. at 0.2-0.3 mm Hg., giving 130 g. of product (87% yield).

Workup

  1. filtration, filtered the reaction mass
  2. washthe residue was washed with acetone
  3. customTo the residue of the evaporation
  4. additionwas added 200 cc of dichloromethane
  5. washthe residue was washed with 100 cc of water
  6. customseparated into two layers
  7. washThe dichloromethane layer was washed with 100 cc of 10% Na2CO3
  8. customseparated again
  9. washwashed again with 100 cc of water
  10. distillationThe main fraction distilled at 103°-106° C. at 0.2-0.3 mm Hg
  11. custom, giving 130 g

Sources & evidence

ORD record
ord-c50366e1aaf143d88d8f60c298b18d14
Source dataset
uspto-grants-1982_08
Patent number
US04345937

Linked notes

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