175229-25-1Relevant articles and documents
Neighboring assistance of a hydroxyl group on manganese dioxide oxidation of benzyl alcohols to lactones
Endo, Katsuya,Takahashi, Hiroyasu,Aihara, Minako
, p. 589 - 615 (1996)
o-Hydroxymethylbenzyl alcohol and o-hydroxyethylbenzyl alcohols have been converted to phthalide and dihydroisocoumarins, very easily and in high yields, by oxidation with non-activated manganese dioxide. In contrast, the reaction of o-hydroxypropylbenzyl alcohol stopped at the aldehyde level, and afforded only a small amount of the corresponding lactone under the same condition. This implies that the first oxidation product, a benzaldehyde, could be oxidized further via a hemiacetal, but the second oxidation to lactone is very much dependent on the ability of stable intramolecular hemiacetal formation, and not on the intermolecular mode at all.
