3,4,5-Trimethoxyhydrocinnamic acid → 5,6,7-Trimethoxy-1-indanone

HRID 1977998

Reaktionsgleichung

Reaktionsgleichung von HRID 1977998
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][CH2:14][C:15]([OH:17])=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]>O>[CH3:12][O:11][C:7]1[CH:6]=[C:5]2[C:4](=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10])[C:15](=[O:17])[CH2:14][CH2:13]2

Komponenten

3

Edukt 1

HCID 648603,4,5-Trimethoxyhydrocinnamic acid

Produkt 1

HCID 6102105,6,7-Trimethoxy-1-indanoneAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3-(3,4,5-trimethoxyphenyl)propionic acid (9.40 g, 39.1 mmol) and polyphosphoric acid (50 g) was stirred for 2 hours at 80° C. To the reaction mixture was added water, which was subjected to extraction with ethyl acetate. The extract solution was washed with brine, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was recrystallized from ethyl acetate/isopropyl ether to give 7.71 g (yield 89%) of the above-titled compound, m.p. 114-115° C.

Aufarbeitung

  1. extractionwas subjected to extraction with ethyl acetate
  2. washThe extract solution was washed with brine, which
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationby distilling off the solvent under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate/isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-be88cccdd0e04b61a3c603911ae5807d
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235789B1

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