Acetic Acid → HCID 21453522, Verbindung

HRID 436248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 436248
[CH3:1][C@@:2]12[CH2:11][CH2:10][CH2:9][C@H:8]([CH3:12])[C:7]1=[CH:6][C:5](=[O:13])[CH2:4][CH2:3]2.CC([O-])(C)C.[K+].C(O)(=O)C.C([O-])(O)=O.[Na+]>C(O)(C)(C)C>[CH3:1][C:2]12[CH2:11][CH2:10][CH2:9][C:8]([CH3:12])=[C:7]1[CH2:6][C:5](=[O:13])[CH2:4][CH2:3]2

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 6428338HCID 6428338, VerbindungHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 21453522HCID 21453522, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

A solution of 2.0 g (11.5 mM) of trans-6,10-dimethyl-bicyclo[4.4.0]dec-1-en-3-one and 12.0 g (ca. 110 mM) of potassium ter-butylate in 75 ml of ter-butanol, has been stirred during 2 hr at room temperature under an inert atmosphere of nitrogen. 400 ml of a 10% aqueous solution of acetic acid were then added thereto and the thus obtained mixture rapidly neutralized with a saturated aqueous solution of NaHCO3. By extraction with ether followed by washing, drying, evaporation and purification by column chromatography on silicagel (elution with CH2Cl2), there were obtained 1.80 g (90% yield) of the desired product. IR (neat) : 1710, 1600 cm-1NMR (CCl4) : 1.20 (3H,s); 1.58 (3H, large s); 2.27 (2H,t,J=5 cps); 3.10 (2H,m) δ ppm MS : M+ = 178 (57); m/e = 163 (100), 123 (45), 93 (42).

Aufarbeitung

  1. extractionBy extraction with ether
  2. washby washing
  3. customdrying
  4. customevaporation and purification by column chromatography
  5. washon silicagel (elution with CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-18ac633e53074bfa8269b451aea65918
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04008184

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