Acetone → HCID 13188177, compound

Participants

Reaction Steps

A mixture of the 2-(4'-benzyloxybutyl)-1,1-ethylenedioxy-2-methylcyclohexane (32.5 g, 0.10 mol), acetone (375 ml), H2O (50 ml) and 0.002 N H2SO4 (125 ml) is refluxed for 18 hours under a nitrogen atmosphere. The reaction mixture is cooled, the acetone is evaporated under reduced pressue and the aqueous layer extracted with ether (3×500 ml). The combined organic layers are washed with satd. NaHCO3 (2×300 ml), satd. NaCl (2×500 ml) and dried (MgSO4). The solvents are removed under reduced pressure and the crude product (29 g) is chromatographed on SilicAR CC-7 (500 g) in hexane. Elution with 5% ethyl acetate/hexane gives 2-(4'-benzyloxybutyl)-2-methylcyclohexanone as a colorless oil (25.4 g, 91%): ir (neat) 1705 cm-1 (CO); nmr (CDCl3) δ1.03 (s, 3H, CH3), 2.35 (m, 2H, OC-- CH2 --CH2), 3.5 (t, 2H, O--CH2 --CH2), 4.44 (s, 2H, O--CH2 --Ph), 7.3 (s, 5H, aromatic).

Provenance & Evidence