A novel synthesis of 1, 4-and 1, 5-dioxepan-2-one lactones was achieved through the regioselective oxidation of 3-(2-hydroxyethoxy) propan-1-ol. Under basic conditions, when 3- (2-hydroxyethoxy) propan-1-ol was oxidized using oxoammonium salts, a quantitative oxidative esterification was observed, resulting in a regioselective lactone ring closure. This oxidation was tailored to afford 1, 4-dioxepan-2-one in very good yield.