Acetic Anhydride → 4-Acetoxy stilbene

HRID 359338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 359338
C(N(CC)CC)C.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1.[CH3:23][C:24](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:25].C(OC(=O)C)(=O)C>C1COCC1>[C:24]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[CH:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:14]=1)(=[O:25])[CH3:23]

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 929714-HydroxystilbeneHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

Produkt 1

HCID 41264694-Acetoxy stilbene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a 4-neck 1 L flask fitted with nechanical agitation, condenser, addition funnel, nitrogen bubbler, and temperature controller was added, in order, THF (450 g), triethylamine (I2.2 g, 0.12 mol), and 4-hydroxy stilbene (19.6 g, 0.10 mol). To this solution at room temperature was slowed added with stirring, via addition funnel, acetic anhdyride (12.3 g, 0.12 mol). When the addition of acetic anhydride was complete, the reaction solution was heated to 60° C. and held at this temperature with stirring for 2 hours. The reaction was cooled to room temperature then THF was removed in vacuo. The resulting residue was diluted with methylene chloride (500 mL) then extracted with 0.1 N HCl (1 ×500 mL), 30% saturated NaHCO3 (1 ×500 mL) and saturated NaCl (1 ×500 mL). The organic layer was dried over anhydrous sodium sulfate then filtered and concentrated in vacuo to give the 4-acetoxy stilbene as a light tan needle-like crystalline powder (22.7 g, 95%).

Aufarbeitung

  1. customTo a 4-neck 1 L flask fitted with nechanical agitation, condenser, addition funnel, nitrogen bubbler, and temperature controller
  2. additionTo this solution at room temperature was slowed added
  3. stirringwith stirring for 2 hours
  4. temperatureThe reaction was cooled to room temperature
  5. customTHF was removed in vacuo
  6. additionThe resulting residue was diluted with methylene chloride (500 mL)
  7. extractionthen extracted with 0.1 N HCl (1 ×500 mL), 30% saturated NaHCO3 (1 ×500 mL) and saturated NaCl (1 ×500 mL)
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. filtrationthen filtered
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0b36e43fe21747cda47b8b77d89123f3
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05001004

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