Sulfuric Acid → 6-Acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman

HRID 263926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 263926
[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([O:18]C)([CH3:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].S(=O)(=O)(O)O>CC(C)=O.O>[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([OH:18])([CH3:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 1118Sulfuric AcidHCID 144156636-Acetoxy-2-methoxy-2,5,7,8-tetramethylchroman

Produkt 1

HCID 144156666-Acetoxy-2-hydroxy-2,5,7,8-tetramethylchromanAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of 6-acetoxy-2-methoxy-2,5,7,8-tetramethylchroman (74.11 g, 266.25 mmol), and concentrated sulfuric acid (2.5 mL) in a mixture of acetone (375 mL) and water 300 mL) was added to a distillation apparatus and warmed at reflux. Distillant was collected until the still head temperature reached 92° C. (about 1.5 h). The slurry was allowed to cool to 70° C. and 240 mL of acetone was added. The resulting mixture was allowed to cool to ambient temperature and the solid that formed was collected filtration. The solid was recrystallized from acetone and dried in a vacuum oven at 60° C. to afford 53.9 g (76.7% yield) of the desired product as a tan solid.

Aufarbeitung

  1. additionwas added to a distillation apparatus
  2. temperaturewarmed
  3. temperatureat reflux
  4. distillationDistillant was collected until the still head temperature
  5. customreached 92° C.
  6. custom(about 1.5 h)
  7. addition240 mL of acetone was added
  8. temperatureto cool to ambient temperature
  9. customthe solid that formed
  10. customwas collected
  11. filtrationfiltration
  12. customThe solid was recrystallized from acetone
  13. customdried in a vacuum oven at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-4ceb346e426640fca1ba9f539afe5f73
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646149

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