Ozonolysis of Olefins VIII [1]. Synthesis of Phenoxyacetaldehydes by Ozonolysis of Allylphenylethers

Article abstract of DOI:10.1007/BF00807397

A new route for the preparation of a series of phenoxyacetaldehydes (2a-j) which are useful intermediates or products, is described. It starts from the easily available allylphenylethers 1a-j which are ozonized at -40°C and further treated with dimethylsulfide to give solutions of the corresponding phenoxyacetaldehydes 2a-j; these are purified by column chromatography. Reaction of 2a-j with 1-methyl-1-phenylhydrazine leads to the corresponding hydrazones 3a-c, 3e-g, 3i, and 3j. The aldehydes can also be transformed into the stable dimethylcetals 4a, 4e, 4h, and 4i by reaction with trimethyl orthoformate.