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Hydrochloric Acid → 5-Methyl-3-Methoxy-5,6,7,8,9,10,11,12-Octahydro-5,11-Methano-Benzocyclodecen-13-One

HRID 1579811
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1579811
[H-].[Na+].Br[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]Br.[CH3:10][CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=2)[CH2:14][CH2:13][C:12]1=[O:23].Cl>C1C=CC=CC=1>[CH3:10][C:11]12[C:12](=[O:23])[CH:13]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][C:20]=31)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 81001,5-DibromopentaneHCID 24758Sodium hydride2×HCID 107977551-Methyl-7-methoxy-2-tetralone

Produkt 1

HCID 214100925-Methyl-3-Methoxy-5,6,7,8,9,10,11,12-Octahydro-5,11-Methano-Benzocyclodecen-13-One

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241
Benzene
Lösungsmittel
3×

Versuchsvorschrift

Oil-free sodium hydride (5.28 g.) in benzene (50 ml.) is added to a stirred mixture of 1,5-dibromopentane (184 g.) and 1-methyl-7-methoxy-2-tetralone (32 g.) in dry benzene (300 ml.). Stirring is continued for 12 hours at 25° and at reflux for an additional 15 hours. The mixture is cooled, sodium hydride (5.8 g.) in 50 ml. benzene added, stirring continued at 25° for 10 hours, and at reflux for 12 additional hours. After cooling excess base is neutralized with concentrated hydrochloric acid and the inorganic solids which precipitate are removed by filtration. Washing and filtrate with saline, drying over sodium sulfate, concentrating and vacuum distilling gives an oil (21 g.), b.p. 160°-190° C. (0.5 mm.) containing 6.5 g. (27 percent) of the title product by vapor phase chromatographed (3 percent OVI, C200- 225- 250).

Aufarbeitung

  1. temperatureat reflux for an additional 15 hours
  2. temperatureThe mixture is cooled
  3. stirringstirring
  4. waitcontinued at 25° for 10 hours
  5. temperatureat reflux for 12 additional hours
  6. temperatureAfter cooling excess base
  7. customthe inorganic solids which precipitate are removed by filtration
  8. washWashing
  9. dry with materialfiltrate with saline, drying over sodium sulfate
  10. concentrationconcentrating
  11. distillationvacuum distilling
  12. customgives an oil (21 g.), b.p. 160°-190° C. (0.5 mm.)
  13. additioncontaining 6.5 g
  14. custom(27 percent) of the title product by vapor phase chromatographed (3 percent OVI, C200- 225- 250)

Quellen und Nachweise

ORD-Eintrag
ord-9c14b37a369648698e816c786bf12c51
Quelldatensatz
uspto-grants-1976_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03931328

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