Sulfuric Acid → 2-Methylideneadamantane

HRID 858912

Reaktionsgleichung

Reaktionsgleichung von HRID 858912
[CH3:1][C:2]1(O)[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.S(=O)(=O)(O)O.C1(C)C=CC=CC=1>O>[CH2:1]=[C:2]1[CH:3]2[CH2:11][CH:7]3[CH2:6][CH:5]([CH2:10][CH:9]1[CH2:8]3)[CH2:4]2

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 1140Toluene2×HCID 1365452-Methyl-2-adamantanol

Produkt 1

HCID 1366842-MethylideneadamantaneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

One liter flask equipped with a Dean-Stark condenser was charged-with 166.3 g (1.0 mol) of 2-methyl-2-adamantanol (supplied by Sigma-Aldrich Co.), 2.0 g (20 mmol) of sulfuric acid and 500 g of toluene. The content was heated to the solvent reflux temperature. While toluene and water produced through the reaction were collected as an azeotrope by the Dean-Stark condenser, the reaction mixture was refluxed for 2 hours. After completion of the reaction, the catalyst was removed by washing the reaction mixture with water and the obtained organic phase was concentrated to dryness to give 152.5 g of white solid 2-methyleneadamantane (purity: 99.0%, yield: 98.0%).

Aufarbeitung

  1. customOne liter flask equipped with a Dean-Stark condenser
  2. temperatureThe content was heated to the solvent
  3. temperaturereflux temperature
  4. customwere collected as an azeotrope by the Dean-Stark condenser
  5. temperaturethe reaction mixture was refluxed for 2 hours
  6. customAfter completion of the reaction
  7. customthe catalyst was removed
  8. washby washing the reaction mixture with water
  9. concentrationthe obtained organic phase was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-14294a07891042589f18ef8b5691167d
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148363B2

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