Sulfuric Acid → HCID 23344098, Verbindung

HRID 916829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916829
[OH:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#N.[OH:14]S(O)(=O)=O.[C:19](=O)([O-])[O-:20].[Na+].[Na+]>CO>[OH:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]([O:20][CH3:19])=[O:14]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 284140323-[(2-Hydroxyethoxy)methyl]benzonitrile

Produkt 1

HCID 23344098HCID 23344098, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 3-[(2-hydroxyethoxy)methyl]benzonitrile (1 g) in MeOH (20 ml) was treated with conc. H2SO4 (10 ml) at 0° C. The solution was then allowed to warm to room temperature before heating at reflux for 10 h. Aqueous sodium carbonate was added to neutralise the cooled solution before extracting with EtOAc. The combined organic layers were then washed with water, dried (MgSO4) and concentrated in vacuo. The residue was then purified by chromatography (Biotage, 90 g) eluting with 40°C.-60° C. petroleum ether-EtOAc (3:2) to give the title compound (650 mg). LCMS RT=2.33 min.

Aufarbeitung

  1. temperaturebefore heating
  2. temperatureat reflux for 10 h
  3. extractionbefore extracting with EtOAc
  4. washThe combined organic layers were then washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was then purified by chromatography (Biotage, 90 g)
  8. washeluting with 40°C.-60° C. petroleum ether-EtOAc (3:2)

Quellen und Nachweise

ORD-Eintrag
ord-d181df1061e84f148cd922d7ca34c8b2
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271197B2

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