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Hydrochloric Acid → methyl 3-(4-methylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylate

HRID 1169320
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1169320
[CH3:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][O:7][C:8]2[CH:19]=[CH:18][C:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.C[O-].[Na+].Cl.[C:26](=O)([O:29]C)[O:27][CH3:28]>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:19]=[CH:18][C:11]3[CH2:12][CH2:13][CH2:14][CH:15]([C:26]([O:27][CH3:28])=[O:29])[C:16](=[O:17])[C:10]=3[CH:9]=2)=[CH:20][CH:21]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 10942334Sodium MethoxideHCID 22990062HCID 22990062, Verbindung

Produkt 1

HCID 22990087methyl 3-(4-methylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylateAusbeute 88 %

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To 3-(4-methylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene (2.67 g, 9.52 mmol) dissolved in dimethyl carbonate (40 ml) was added sodium methoxide (2.57 g, 47.6 mmol), and the resulting mixture was stirred at reflux with heating (110° C.) for 6 hours. The reaction mixture was mixed with 1 N hydrochloric acid (60 ml) under ice cooling and was concentrated under reduced pressure to remove the organic solvent, and then the aqueous layer was extracted with ethyl acetate (30 ml×3). The combined organic layers were dried with anhydrous magnesium sulfate and were then concentrated under reduced pressure, and the residue was subjected to column chromatography (silica gel: 40 g, ethyl acetate/hexane=1/30). The objective fractions were concentrated under reduced pressure to obtain methyl 3-(4-methylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylate (2.84 g, 8.39 mmol, 88%).

Aufarbeitung

  1. temperatureat reflux
  2. concentrationwas concentrated under reduced pressure
  3. customto remove the organic solvent
  4. extractionthe aqueous layer was extracted with ethyl acetate (30 ml×3)
  5. dry with materialThe combined organic layers were dried with anhydrous magnesium sulfate
  6. concentrationwere then concentrated under reduced pressure
  7. concentrationThe objective fractions were concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c265f7205f544f979fa75dbb6d141209
Quelldatensatz
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06627651B1

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