3-Chloro-2-methyl-1-propene → alpha-Methallyl-alpha,3,3-trimethyl-5-norbornene-2-methanol

HRID 26187

Reaktionsgleichung

Reaktionsgleichung von HRID 26187
[Mg].[CH2:2](Cl)[C:3](=[CH2:5])[CH3:4].[C:7]([CH:10]1[C:15]([CH3:17])([CH3:16])[CH:14]2[CH2:18][CH:11]1[CH:12]=[CH:13]2)(=[O:9])[CH3:8].[Cl-].[NH4+]>C(OCC)C>[CH2:2]([C:7]([CH3:8])([CH:10]1[C:15]([CH3:16])([CH3:17])[CH:14]2[CH2:18][CH:11]1[CH:12]=[CH:13]2)[OH:9])[C:3](=[CH2:5])[CH3:4]

Komponenten

6

Edukt 4

HCID 112413-Chloro-2-methyl-1-propeneHCID 25517Ammonium ChlorideHCID 1625111-(3,3-Dimethylbicyclo(2.2.1)hept-5-en-2-yl)ethan-1-oneHCID 5462224Magnesium

Produkt 1

HCID 21319801alpha-Methallyl-alpha,3,3-trimethyl-5-norbornene-2-methanolAusbeute 106,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Into a 1 liter reaction flask equipped with a reflux condenser, thermometer, stirrer, dropping funnel and nitrogen inlet tube are placed 12 g (0.5 moles) of magnesium turnings and 250 cc anhydrous diethyl ether. Over a 2 hour period, 45.3 g (0.5 moles) of methallyl chloride is added. The Grignard solution is stirred for 1/2 hour and 28 g of 2-acetyl-3,3-dimethyl-5-norbornene is added over a 20 minute period. The mixture is stirred at reflux for 1/2 hour and then is hydrolyzed by the addition of saturated ammonium chloride solution. The organic layer is washed with water and dried over magnesium sulfate. The mixture is then filtered and the solvent evaporated to yield 40 g of an oil, which is then fractionated on a micro Vigreux column after adding thereto 5 g Primol® and a trace quantity of Ionox®.

Aufarbeitung

  1. customInto a 1 liter reaction flask
  2. customequipped with a reflux condenser
  3. customthermometer, stirrer, dropping
  4. customfunnel and nitrogen inlet tube are placed
  5. stirringThe mixture is stirred
  6. temperatureat reflux for 1/2 hour
  7. washThe organic layer is washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationThe mixture is then filtered
  10. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-8d98939ba4254bfdae96417e380f1482
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04148826

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