Efficient and selective reduction protocols of the 2,2-dimethyl-1,3-benzodioxan-4-one functional group to readily provide both substituted salicylaldehydes and 2-hydroxybenzyl alcohols.
Two complementary procedures have been developed that selectively allow for the synthesis of either substituted salicylaldehydes or the corresponding 2-hydroxylbenzyl alcohols upon treatment of the 2,2-dimethyl-1,3-benzodioxan-4-one functional group with DIBAL-H or LAH, respectively.
Bajwa
Naval
N
Department of Chemistry, University of Alabama, 500 Campus Drive, Tuscaloosa, Alabama 35487-0336, USA.
Jennings
Michael P
MP
D000447:Aldehydes / Q000138:chemical synthesis*; D052117:Benzodioxoles / Q000737:chemistry; D001592:Benzyl Alcohols / Q000138:chemical synthesis*; D004146:Dioxanes / Q000737:chemistry; D010084:Oxidation-Reduction
D000447:Aldehydes; D052117:Benzodioxoles; D001592:Benzyl Alcohols; D004146:Dioxanes; C013243:salicylaldehyde