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Acetic Acid → 2-(3-Hydroxy-naphthalen-1-yloxy)-2-methyl-propionic acid ethyl ester

HRID 1727006
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1727006
[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([O:19]C(OC)=O)[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].[O-]CC.[Na+].CC(O)=O>CCO>[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([OH:19])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 2723922Sodium ethoxideHCID 690371532-(3-Methoxycarbonyloxy-naphthalen-1-yloxy)-2-methyl-propionic acid ethyl ester

Produkt 1

HCID 690411092-(3-Hydroxy-naphthalen-1-yloxy)-2-methyl-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

1.35 g (4.1 mmol) of 2-(3-methoxycarbonyloxy-naphthalen-1-yloxy)-2-methyl-propionic acid ethyl ester was dissolved in 30 ml of EtOH and cooled down to 5° C.; while stirring, 1.66 ml=1.45 g (4.5 mmol) of a solution of sodium ethoxide (21% in EtOH) was added and the reaction mixture then warmed up to ambient temperature. After 1 hour, it was poured into crashed ice/MeCl2, the pH was adjusted to 5-6 with AcOH (1N) and the reaction mixture was subsequently extracted twice with MeCl2; the organic phases were washed with water, dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (SiO2, gradient of MeCl2/MeOH) to finally give 0.95 g of the title compound as light brown oil.

Aufarbeitung

  1. temperaturethe reaction mixture then warmed up to ambient temperature
  2. additionit was poured
  3. extractionthe reaction mixture was subsequently extracted twice with MeCl2
  4. washthe organic phases were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was purified by flash chromatography (SiO2, gradient of MeCl2/MeOH) to finally give 0.95 g of the title compound as light brown oil

Quellen und Nachweise

ORD-Eintrag
ord-cca1b42930cd47b2836738145e6e8fe1
Quelldatensatz
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07495001B2

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