Acetic Acid → HCID 10657149, Verbindung

HRID 322959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 322959
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N+:17](CC)([O-])=O.C([O-])(=O)C.[Na+].C(O)(=O)C>O>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:17]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 6587NitroethaneHCID 517045Sodium AcetateHCID 10537643HCID 10537643, Verbindung

Produkt 1

HCID 10657149HCID 10657149, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-hydroxy-4-(3-thienylmethoxy)benzaldehyde (7.7 g), nitroethane (4.74 mL), sodium acetate (5.4 g) and glacial acetic acid (6.6 mL) is heated at reflux for 14 hours. The mixture is then cooled, diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts are washed with saturated aqueous sodium bicarbonate solution (3×50 mL), dried over magnesium sulphate, and concentrated in vacuo. The resulting residue is subjected to flash chromatography on silica gel, eluting with a mixture of ethyl acetate and pentane (3:7 v/v), to give 2-hydroxy-4-(3-thienylmethoxy)benzonitrile (7.6 g), in the form of a pale yellow solid.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 14 hours
  3. temperatureThe mixture is then cooled
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washThe combined organic extracts are washed with saturated aqueous sodium bicarbonate solution (3×50 mL)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. washeluting with a mixture of ethyl acetate and pentane (3:7 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-d5e79df5a6704ccfa8e8c1028b3e4732
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211234B1

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