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Citric Acid → 2-(Benzyloxy)-5-(morpholin-4-yl)benzoic acid

HRID 454509
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 454509
[OH-].[Na+].C(O)C.[CH2:6]([O:13][C:14]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:20][C:15]=1[C:16]([O:18]C)=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)(=O)C>[CH2:6]([O:13][C:14]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:20][C:15]=1[C:16]([OH:18])=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 66990981Methyl 2-(benzyloxy)-5-(morpholin-4-yl)benzoate

Produkt 1

HCID 669907782-(Benzyloxy)-5-(morpholin-4-yl)benzoic acidAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857
Ethyl Acetate
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A 4 mol/L aqueous solution of sodium hydroxide (0.3 mL) was added to an ethanol (2.1 mL) solution of the obtained methyl 2-(benzyloxy)-5-(morpholin-4-yl)benzoate (0.26 g), followed by stirring at 50° C. for 1 hour. The reaction mixture was cooled to room temperature, and then a 10% aqueous solution of citric acid and ethyl acetate were sequentially added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.17 g of 2-(benzyloxy)-5-(morpholin-4-yl)benzoic acid as a white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionDiisopropyl ether was added to the obtained residue
  7. filtrationthe solid substance was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-a5d0d94497434f24a4e53fcaf1aedbdb
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492582B2

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