4,4-Dimethyl-1,2,3,4-tetrahydronaphthalen-1-ol → 1,2-Dihydro-1,1-dimethylnaphthalene

HRID 1654330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1654330
[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5](O)[CH2:4][CH2:3]1>C(O)(=O)C(O)=O.O>[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH2:3]1

Komponenten

4

Edukt 1

HCID 126430324,4-Dimethyl-1,2,3,4-tetrahydronaphthalen-1-ol

Produkt 1

HCID 127728391,2-Dihydro-1,1-dimethylnaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 971Oxalic AcidLösungsmittel

Versuchsvorschrift

A mixture of 1,2,3,4-tetrahydro-4,4-dimethyl-1-naphthol (9.6 g, 54.5 mmoles) in 20% aqueous oxalic acid was stirred and heated to reflux for 5 hours. After cooling, the reaction mixture was diluted with one volume of water and then extracted with one volume of ether. The aqueous layer was extracted again with one volume of ethyl acetate and the combined organic phases were dried over magnesium sulfate, filtered, and evaporated under reduced pressure to leave an oil which was purified using silica gel column chromatography, eluting with ethyl acetate:hexane (0.1:49.9) to give 1,2-dihydro-1,1-dimethylnaphthalene as a colorless oil. (4.76 g, 55%).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. temperatureAfter cooling
  4. extractionextracted with one volume of ether
  5. extractionThe aqueous layer was extracted again with one volume of ethyl acetate
  6. dry with materialthe combined organic phases were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto leave an oil which
  10. customwas purified
  11. washeluting with ethyl acetate:hexane (0.1:49.9)

Quellen und Nachweise

ORD-Eintrag
ord-9ce290f6e2e34ca9a42b649992dc0a42
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05405851

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