Background: A one-pot method for the preparation of the corresponding alkoxy acetic acids
by low-temperature ozonolysis of allyl ethers/esters followed by treatment with semicarbazide hydrochloride
has been suggested. The reaction occurs via formation of acetoxyhydroperoxide, subsequent
reduction of which depends on the process temperature and the nature of the starting substrate.
Objective: The article is aimed at the development of one-pot method for obtaining practically important
alkoxy acetic acids, because the ozonolytic cleavage of a С=С double bond is the key step in full syntheses
of many biologically active compounds.
Methods: We used a low temperature ozonolysis of functionally substituted olefins in the system acetic
acid-methylene dichloride followed by reduction of semicarbazide hydrochloride. To create a method
we have used available allyl ethers/esters as starting materials.
Results: We investigated reaction of the peroxide products of ozonolysis of monoallyl ethers, ester and
diallyl ethers in an АсОН/CH2
mixture on treatment with semicarbazide hydrochloride at various
temperatures. We have discovered that the selectivity of reduction of acetoxyhydroperoxide formed at
the first stage depends both on the process temperature and on the nature of the starting substrate. A decrease
in temperature favors acid hydrolysis and formation of a carboxylic acid.
Conclusion: We have proposed a simple and highly efficient one-pot method for the preparation alkoxy
acetic acids without isolation of intermediate peroxides.