Gallic Acid → Benzoic acid, 3,4,5-tris(acetyloxy)-

HRID 1614280

Reaktionsgleichung

Reaktionsgleichung von HRID 1614280
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.C(O[C:17](=[O:19])[CH3:18])(=O)C.S(=O)(=O)(O)O>O>[C:4]([O:5][C:4]1[CH:3]=[C:2]([CH:10]=[C:8]([O:9][C:17](=[O:19])[CH3:18])[C:6]=1[O:7][C:6](=[O:7])[CH3:8])[C:1]([OH:12])=[O:11])(=[O:5])[CH3:3]

Komponenten

5

Edukt 3

HCID 370Gallic AcidHCID 1118Sulfuric AcidHCID 7918Acetic Anhydride

Produkt 1

HCID 95088Benzoic acid, 3,4,5-tris(acetyloxy)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

In a one liter round bottom flask, with a magnetic stirrer, were combined gallic acid (170.1 g, 1.0 mole) and acetic anhydride (566 ml, 6 moles). The slurry was stirred as sulfuric acid (1.06 ml) was added. The temperature rose rapidly from 21° C. to 75° C. over about 1 minute and the slurry became a clear yellow solution. The mixture was stirred and allowed to cool to ambient temperature over 20 minutes. The solution was then poured into a stirred, four liter Erlenmeyer flask containing three liters of water. After 2.5 hours, white crystalline product was isolated by filtration and washed 3 times with 500 milliliters of water. The product was dried in a stream of air for 3 hours and then vacuum dried overnight. Yield was 262 grams, which was 88% of theoretical yield. Melting point was 166°-168° C. NMR conducted as in the preceeding preparation, but using (CDCl3) gave as peaks, in ppm: 2.30 (s, 9H), 7.86 (s, 2H), 11.95 (broad, 1H).

Aufarbeitung

  1. customIn a one liter round bottom flask, with a magnetic stirrer, were combined
  2. additionwas added
  3. additionThe solution was then poured into a stirred, four liter Erlenmeyer flask
  4. waitAfter 2.5 hours
  5. customwhite crystalline product was isolated by filtration
  6. washwashed 3 times with 500 milliliters of water
  7. customThe product was dried in a stream of air for 3 hours
  8. customvacuum dried overnight
  9. customNMR conducted as in the preceeding preparation
  10. customgave as peaks, in ppm

Quellen und Nachweise

ORD-Eintrag
ord-d9ab074afcee46d18c5b5e135f97ac80
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05196502

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