m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

Participants

Reaction Steps

A solution of 30.4 g of 1,2-O-isopropylidene-3-O-n-propyl-5,6-dideoxy-6-phenyl-α-D-xylo-cis-hex-5-enofuranose and 22.2 g of m-chloroperbenzoic acid (85% strength) in 250 ml of methylene chloride is stirred at room temperature for 15 hours with the exclusion of moisture. The m-chlorobenzoic acid which has formed is then filtered off and the filtrate is washed with 1 N sodium hydroxide solution, water, 10% strength iron-II sulphate solution, 1 N sodium hydroxide solution and again with water. After drying the methylene chloride phase over magnesium sulphate and evaporating and crystallising the resulting residue, pure 1,2-O-isopropylidene-3-O-n-propyl-5,6-anhydro-6-C-phenyl-β-L-glycero-L-ido-hexafuranose with a melting point of 84°-85° and an optical rotation [α]D20 =-120°±1° (c=1.14 in choroform) is obtained.

Provenance & Evidence