Anthranilic Acid → 1,4-Ethanonaphthalene, 1,4-dihydro-

HRID 10152

Reaktionsgleichung

Reaktionsgleichung von HRID 10152
[C:1](O)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)N.[CH:11]1[CH2:16]CC=[CH:13][CH:12]=1.N(O[CH2:20]CC(C)C)=O>O1CCCC1>[CH:2]12[CH2:8][CH2:7][CH:6]([C:5]3[C:3]1=[CH:13][CH:12]=[CH:11][CH:16]=3)[CH:20]=[CH:1]2

Komponenten

5

Edukt 3

HCID 227Anthranilic AcidHCID 8053Isoamyl NitriteHCID 116051,3-Cyclohexadiene

Produkt 1

HCID 1389941,4-Ethanonaphthalene, 1,4-dihydro-Ausbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A THF solution of 1 g (7.3 mmol) of anthranilic acid was dropped into a mixed solution under reflux of 0.77 ml (8.0 mmol) of 1,3-cyclohexadiene, 1.1 ml of isoamyl nitrite and 50 ml of tetrahydrofuran. Then, the resultant solution was heated and refluxed for 2 hours to remove THF, extracted with chloroform, washed with distilled water and saturated saline, dried with anhydrous sodium sulfate and purified with silica gel column-chromatography-(chloroform) to obtain 1,4-dihydro-1,4-ethanonaphthalene (0.89 g, 5.7 mmol, yield: 78%).

Aufarbeitung

  1. temperaturerefluxed for 2 hours
  2. customto remove THF
  3. extractionextracted with chloroform
  4. washwashed with distilled water and saturated saline
  5. dry with materialdried with anhydrous sodium sulfate
  6. custompurified with silica gel column-chromatography-(chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-a17440283c1b4d1dba9b75e78b2c71b4
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094625B2

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