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Benzyl Bromide → 5-(Benzyloxy)-1,2,3,4-tetrahydronaphthalene

HRID 1719199
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1719199
[C:1]1([OH:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O.CCOCC>[CH2:18]([O:11][C:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 682585,6,7,8-Tetrahydro-1-naphthol

Produkt 1

HCID 226476065-(Benzyloxy)-1,2,3,4-tetrahydronaphthaleneAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittel
HCID 3283
Diethyl Ether
Lösungsmittel

Versuchsvorschrift

5,6,7,8-tetrahydro-1-naphthol (5.9 g, 39mM) was added to a suspension of potassium carbonate (8.3 g, 60mM) in acetone (100 ml) and heated under reflux for 0.5 hour. Benzyl bromide (7.5 g, 43.8mM) was then added and the mixture was heated under reflux for a further 3 days with stirring. The resulting suspension was filtered and the filtrate was evaporated under reduced pressure to give an oil. This oil was dissolved in ether, washed with water, dried (sodium sulphate) and evaporated to giving an oil which was distilled under high vacuum to give the benzyl ether (3) (9.4 g, b.p. 170°-176° C. at 0.8 mm Hg).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 0.5 hour
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for a further 3 days
  5. filtrationThe resulting suspension was filtered
  6. customthe filtrate was evaporated under reduced pressure
  7. customto give an oil
  8. washwashed with water
  9. dry with materialdried (sodium sulphate)
  10. customevaporated
  11. customto giving an oil which
  12. distillationwas distilled under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ac8df157aa654bf7a11ea1c6e40d18fe
Quelldatensatz
uspto-grants-1985_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04539319

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