Acetic Acid → HCID 21453522, compound

Participants

Reaction Steps

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).

Provenance & Evidence