Morpholine → Chroman-2-ol

HRID 2226624

Reaktionsgleichung

Reaktionsgleichung von HRID 2226624
C(C1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[OH:14])(=O)C.C1C2CC(=[O:22])C(C2)C1.N1CCOCC1>C1(C)C=CC=CC=1>[O:22]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH:5]1[OH:14]

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 10345Bicyclo(2.2.1)heptan-2-oneHCID 684551-(2-Hydroxy-1-naphthyl)ethan-1-one

Produkt 1

HCID 11171070Chroman-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution was prepared by dissolving 10 g (0.054 mole) of 1-acetyl-2-naphthol, 6.6 g (0.06 mole) of norcamphor and 8.7 g (0.10 mole) of morpholine in 300 cc of toluene, and the solution was boiled for 5 hours and water was separated. After termination of the reaction toluene was removed under reduced pressure, and the remaining chromanone compound was recrystallized from acetone, and the chromanon compound was dissolved in 200 cc of methanol and lithium aluminum hydride was added to the solution to form a chromanol compound. Then, 6.49 g of this chromanol compound was heated at 170° to 180° C. together with anhydrous copper sulfate in a carbon dioxide current for 10 minutes and the obtained brown viscous liquid was purified by the chromatography on silica gel to obtain 5.1 g of a chromene compound represented by the following formula: ##STR68##

Aufarbeitung

  1. customA solution was prepared
  2. customwater was separated
  3. customAfter termination of the reaction toluene
  4. customwas removed under reduced pressure
  5. customthe remaining chromanone compound was recrystallized from acetone
  6. dissolutionthe chromanon compound was dissolved in 200 cc of methanol
  7. additionlithium aluminum hydride was added to the solution

Quellen und Nachweise

ORD-Eintrag
ord-b1518844e3324af1b0ab481d4df0c8b2
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05349065

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