Acetone → 2-Allyloxy-1,4-dinitrobenzene

HRID 428801

Reaktionsgleichung

Reaktionsgleichung von HRID 428801
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[OH:13])([O-:3])=[O:2].[CH2:14](Br)[CH:15]=[CH2:16].CC(C)=O.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[CH2:16]([O:13][C:5]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH:15]=[CH2:14]

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 94922,5-DinitrophenolHCID 11430Potassium Carbonate

Produkt 1

HCID 222514472-Allyloxy-1,4-dinitrobenzeneAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A mixture of 2,5-dinitrophenol (7.36 g, 40 mmol), allyl bromide (4.84 g, 40 mmol), acetone (75 mL), 1methylpyrrolidinone (3 mL) and potassium carbonate (11.0 g, 80 mmol) was heated to 50-60° C. for 22 h. The mixture was cooled to room temperature and filtered and the solid rinsed with ethyl acetate. The filtrate was concentrated and recrystallized from isopropanol-hexane (1:1) to give 2-allyloxy-1,4-dinitrobenzene as yellow crystals (8.36 g, mp 66.5-68° C.).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. washthe solid rinsed with ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. customrecrystallized from isopropanol-hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-08d86f4adda84541a2a504177aa8cdc6
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313348B1

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