9-Amino-12-hydroxy-9,10-dihydro-9,10-ethanoanthracene → 9,10-Dihydro-9,10-methanoanthracene-9-carboxaldehyde

HRID 27948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 27948
N[C:2]12[CH:17]([OH:18])[CH2:16][CH:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=31)[C:8]1[C:3]2=[CH:4][CH:5]=[CH:6][CH:7]=1.N([O-])=O.[Na+]>C(O)(=O)C.O>[CH:17]([C:2]12[CH2:16][CH:9]([C:8]3[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=31)[C:10]1[C:15]2=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:18]

Komponenten

5

Edukt 2

HCID 124041369-Amino-12-hydroxy-9,10-dihydro-9,10-ethanoanthraceneHCID 23668193Sodium Nitrite

Produkt 1

HCID 124041419,10-Dihydro-9,10-methanoanthracene-9-carboxaldehydeAusbeute 100,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of 9-amino-12-hydroxy-9,10-dihydro-9,10-ethanoanthracene (3.0 g) in acetic acid (240 ml) was added a solution of sodium nitrite (6.7 g) in water (120 ml) at 2°-5° C., and the resulting mixture was stirred at the same temperature for 1 hour and at 95°-105° C. for 5 hours. The reaction mixture was diluted with water and extracted with benzene. The benzene layer was washed with water, dried over sodium sulfate and evaporated to dryness to give crude crystals of 9-formyl-9,10-dihydro-9,10-methanoanthracene (2.8 g), which were recrystallized to give colorless crystals (2.45 g). M.P. 99°-100° C. Further, purification by recrystallization gave analytically pure 9-formyl-9,10-dihyfro-9,10-methanoanthracene, M.P. 102.5° C.

Aufarbeitung

  1. extractionextracted with benzene
  2. washThe benzene layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-e4ea9ed5834c464ba120c7a9f98353ef
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04224344

Notizen zur Reaktion

Wird geladen…