HCID 12548507, Verbindung → 4,4-Di(hydroxymethyl)bicyclo(2.2.1)heptene

HRID 67941

Reaktionsgleichung

Reaktionsgleichung von HRID 67941
C([O:3][C:4]([C:6]1([C:13](OCC)=[O:14])[CH2:11][CH:10]2[CH2:12][CH:7]1[CH:8]=[CH:9]2)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:3][CH2:4][C:6]1([CH2:13][OH:14])[CH2:11][CH:10]2[CH2:12][CH:7]1[CH:8]=[CH:9]2

Komponenten

4

Edukt 2

HCID 12548507HCID 12548507, VerbindungHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 1109174,4-Di(hydroxymethyl)bicyclo(2.2.1)hepteneAusbeute 140,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Into a solution containing 2,2-bisethoxycarbonyl-5-norbornene (10 g) in dry tetrahydrofuran (100 ml) was added a mixture of lithium aluminum hydride (4.3 g) and dry tetrahydrofuran (100 ml) with stirring at room temperature. The reaction mixture was refluxed for 2 hours. After consumption of excess LiAlH4 by addition of water, the reaction mixture was concentrated to give a residue, which was extracted with chloroform. The extract was washed with a saturated NaCl solution, dried and concentrated to give as a solid substance 2,2-bishydroxymethyl-5-norbornene (Compound No. 21-1) (9.1 g), M.P., 108°-110° C. (recrystallization from isopropanol). IRνmaxNujol (cm-1): 3300, 2950, 1020.

Aufarbeitung

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for 2 hours
  3. customAfter consumption of excess LiAlH4
  4. additionby addition of water
  5. concentrationthe reaction mixture was concentrated
  6. customto give a residue, which
  7. extractionwas extracted with chloroform
  8. washThe extract was washed with a saturated NaCl solution
  9. customdried
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b474c9fa173143b3bd54aab6cb69a1fa
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04347254

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