2-Nitrophenol → 1-Nitro-2-propoxybenzene

HRID 1447738

Reaktionsgleichung

Reaktionsgleichung von HRID 1447738
[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]

Komponenten

5

Edukt 3

HCID 69472-NitrophenolHCID 78401-BromopropaneHCID 11430Potassium Carbonate

Produkt 1

HCID 5874971-Nitro-2-propoxybenzeneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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 vaccum. The main fraction distilled at 103°-106° C. at 0.2-0.3 mm Hg., giving 130 g. of product (87% yield).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-debd3b32cdbb480285d0980701c63e8b
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04178167

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