Metaperiodic acid → HCID 13608882, compound

Participants

Reaction Steps

Periodic acid (excess) was added to a solution of 2-chloromethylhexadecan-1,2-diol (23a, 0.021 g, 0.068 mmole) in wet ether (15 ml). The progress of the reaction was followed by TLC (30% ethyl acetate-hexane) and within 70 minutes, the diol 23a was completely transformed to a new, nonpolar product. Additional ether (15 ml) was added and the organic solution was washed with water (2×) and brine. The ether layer was dried (MgSO4), filtered, and concentrated, leaving 0.017 g (0.062 mmole, 91%) of a crystalline material. Recrystallization from methanol gave 0.009 g of 1-chlorohexadecan-2-one (25), mp. 52.5°-53.5° C. (lit.16 mp., 52°-52.5° C.).

Provenance & Evidence