Selective oxidation of secondary over primary hydroxyl group

摘要

Selective oxidation of oligoethylene glycol ether methyl 12(13)-hydroxy-13(12)-[11-hydroxy-3,6,9-trioxa-undecyl-1-oxy]-octadec-9-enoate 3 has been studied using pyridinium chlorochromate (PCC).The reaction has resulted in the formation of methyl 12(13)-oxo-13(12)-[11-hydroxy-3,6,9-trioxa-undecyl-l-oxy]-octadec-9-enoate 5 as an unexpected product wherein only the secondary hydroxyl group has been oxidized while the primary hydroxyl group has remained intact.