Base-Catalyzed Alkylation of 2-Naphthol with Glyoxal

Article abstract of DOI:10.1021/jo00010a029

Alkylation of potassium 2-naphthyl oxide with glyoxal in aqueous media formed 1,2-dihydronaphtho<2,1-b>furan-1,2-diol (1).Without isolation of 1, acidification of this reaction mixture with aqueous HCl led to three products, i.e., the lactone of (2-hydroxy-1-naphthyl)acetic acid (2), the hemiacetal of bis(2-hydroxy-1-naphthyl)acetaldehyde (3), and the corresponding acetal (4).Mutual interconversions of 1 and these three products revealed the reaction pathway and the mechanisms of formation of the lactone and the acetal.