Water → Bicyclo[3.2.1]octan-8-ol, 1,5,8-trimethyl-

HRID 1380713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1380713
[CH3:1][C:2]12[C:9](=[O:10])[C:6]([CH3:11])([CH2:7][CH2:8]1)[CH2:5][CH2:4][CH2:3]2.[CH3:12][Li].O>COC.C(OCC)C>[CH3:11][C:6]12[C:9]([CH3:12])([OH:10])[C:2]([CH3:1])([CH2:8][CH2:7]1)[CH2:3][CH2:4][CH2:5]2

Komponenten

6

Edukt 3

HCID 962WaterHCID 895551,5-Dimethylbicyclo(3.2.1)octan-8-oneHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 163417Bicyclo[3.2.1]octan-8-ol, 1,5,8-trimethyl-Ausbeute 73,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8254Dimethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 45,8 g (0,3 mole) of 1,5-dimethyl-bicyclo[3.2.1]octane-8-one in 150 ml dried dimethylether at boiling temperature 250 ml (178 g) of a 5% solution of methyl lithium (4 mole) in diethylether were dropwise added under stirring. After 1 h of stirring at boiling temperature about 50 ml water were dripped in followed by extraction with diethylether. The combined organic phases were dried over Na2SO4, evaporated under vacuum and distilled which resulted in 37 g (73%) of 8 in form of a colorless oil having a boiling point (1 mm) of 74° C. IR (as oil film): 3500 cm-1 (O--H).--NMR (CCl4): δ=0,87, s, 6H (1,5-CH3), 1,05, s, 3H (8-CH3) 1.5 ppm, br.s, 4H (6,7-CH2).--MS: m/e (%)=168 (33, M+), 153 (28), 150 (29). 135 (46), 125 (30), 124 (18), 123 (31, 122 (20), 121 (42), 111 (11), 110 (10), 109 (16), 108 (19), 107 (85), . . . , 43 (100).C11H20O (M=168,27).

Aufarbeitung

  1. extractionin followed by extraction with diethylether
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. customevaporated under vacuum
  4. distillationdistilled which

Quellen und Nachweise

ORD-Eintrag
ord-f7ec33d4863f4c6791084f24050f656b
Quelldatensatz
uspto-grants-1986_04
Patentnummer
US04582945

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