SYNTHESIS OF 3-HYDROXYALDEHYDES 3-HYDROXY ACETALS AND 3-HYDROSY ETHERS FROM 2-ALKOXYOXETANES

2-Alkoxyoxetanes have been found to react quantitatively under mild conditions with water to give 3-hydroxyaldehydes, with primary, secondary, or tertiary alcohols or phenols to give 3-hydroxy acetals, and with Grignard reagents and lithium aluminum hydride to yield 3-hydroxy ethers. These reactions may be carried out selectively in the presence of the isomeric 3-alkoxyoxetanes which are obtained together with 2-alkoxyoxetanes from the photochemical cycloaddition of carbonyl compounds to vinyl ethers. Hydrolysis of some 3-alkoxyoxetanes to substituted glycerine α-monoethers is also described. © 1969, American Chemical Society. All rights reserved.