m-Chloroperbenzoic acid → HCID 13188178, compound

Participants

Reaction Steps

A solution of 2-(4'-benzyloxybutyl)-2-methylcyclohexanone (25.2 g, 0.092 mol), sodium acetate (8.2 g, 0.1 mol), m-chloroperoxybenzoic acid 85% (24.2 g, 0.12 mol) and distilled methylene chloride (1200 ml) is heated at reflux under a nitrogen atmosphere for 7 hours. The solution is cooled and filtered and the filtrate is washed with satd. NaHCO3, satd. NaCl, and dried (MgSO4). The solvent is removed under reduced pressure and the crude product (30.6 g) is chromatographed on SilicAR CC-7 (600 g) in hexane. Elution with 20% ethyl acetate/hexane gives 7-(4'-benzyloxybutyl)-7-methyl-1-oxa-cycloheptan-2-one (6) as a clear light yellow oil (24.2 g, 91%): ir (neat) 1720 cm-1 (lactone); nmr (CDCl3) δ1.42 (s, 3H, CH3), 2.64 (m, 2H, OC--CH2 --CH2), 3.50 (m, 2H, O--CH2 --CH2), 4.50 (s, 2H, O--CH2 --Ph), 7.32 (s, 5H, aromatic).

Provenance & Evidence