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Acetic Acid → 5-(Benzyloxy)-2-(methoxycarbonyl)-1-tetralone

HRID 1271265
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1271265
[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[CH2:9]([O:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH2:19][CH2:20][CH2:21][C:22]2=[O:27])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)(=O)C>O1CCOCC1.O>[CH2:9]([O:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH2:19][CH2:20][CH:21]([C:3]([O:6][CH3:7])=[O:8])[C:22]2=[O:27])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 105869155-(Benzyloxy)-1,2,3,4-tetrahydronaphthalen-1-one

Produkt 1

HCID 229320015-(Benzyloxy)-2-(methoxycarbonyl)-1-tetraloneAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
82.5 °C

Versuchsvorschrift

Under an argon atmosphere, 2.09 g of 60% sodium hydride was suspended in 30 ml of anhydrous dioxane and 11.51 g of dimethyl carbonate was added. While stirring with heating in an oil bath at 80 to 85° C., a solution of 6.58 g of 5-(benzyloxy)-1-tetralone in 15 ml of dioxane was added dropwise over about one hour. After stirring for one hour, the reaction solution was ice-cooled and 52 ml of an aqueous 1N acetic acid solution was added dropwise. The reaction solution was diluted with water, extracted with diethyl ether, washed with water and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 7.95 g of the desired compound as a pale yellow oily substance.

Aufarbeitung

  1. stirringAfter stirring for one hour
  2. temperaturecooled
  3. extractionextracted with diethyl ether
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-435f2a26a0204e24ab77c276ef29e0fd
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07205302B2

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