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

HRID 27949Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 27949
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+]>Cl.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 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 9-amino-12-hydroxy-9,10-dihydro-9,10-ethanoanthracene (50 mg) in conc. hydrochloric acid (2 ml) and water (2 ml) was added a solution of sodium nitrite (112 mg) in water (1.0 ml) at 0° C. The resulting mixture was stirred at 0° C. for 1 hour and at room temperature 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 (35 mg).

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-d9eccbb1cef34c37ab2683206d182317
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04224344

Notizen zur Reaktion

Wird geladen…