Potassium Iodide → 2-Methyl-3-(3-methyl-2-nitrophenoxy)-1-propene

HRID 363795

Reaktionsgleichung

Reaktionsgleichung von HRID 363795
[CH3:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Cl)[C:19](=[CH2:21])[CH3:20].[I-].[K+]>CS(C)=O.O>[CH3:20][C:19]([CH2:21][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[N+:9]([O-:11])=[O:10])=[CH2:18]

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 210263-Methyl-2-nitrophenol

Produkt 1

HCID 108222032-Methyl-3-(3-methyl-2-nitrophenoxy)-1-propeneAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 20.0 grams (0.130 mole) of 3-methyl-2-nitrophenol and 22.5 grams (0.163 mole) of potassium carbonate in 200 mL of dimethyl sulfoxide was stirred, and 15.3 mL (0.156 mole) of methallyl chloride was added dropwise during a five minute period. Upon completion of addition, 5.4 grams (0.033 mole) of potassium iodide was added in one portion. The reaction mixture was then stirred at ambient temperature for about 18 hours. After this time the reaction mixture was poured into 500 mL of water. The mixture was then extracted with two 200 mL portions of diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 27.0 grams of 2-methyl-3-(3-methyl-2-nitrophenoxy)-1-propene. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. additionwas added in one portion
  2. stirringThe reaction mixture was then stirred at ambient temperature for about 18 hours
  3. extractionThe mixture was then extracted with two 200 mL portions of diethyl ether
  4. dry with materialThe combined extracts were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-838241d71b10447da5f7616eb996d3f1
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05874579

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