The oxidative cleavage of vicinal diols to the corresponding aldehydes or ketones is a highly useful transformation in organic synthesis. Traditional methods for carrying out this transformation encompass the use of lead tetraacetate or periodates, that show obvious disadvantages such as the high toxicity of lead tetraacetate and its use in stoichiometric amounts, that implies the generation as byproduct of big amounts of lead diacetate, also toxic. On the other hand, the use of periodates shows limitations in the scope, as ditertiary diols cannot be used.
Therefore, a new method has been developed that uses as oxidant dimethyl sulfoxide, easily accessible and environmentally friendly, for the efficient synthesis of aldehydes and ketones by oxidative cleavage of 1,2-diols.
New and innovative aspects
Dimethyl sulfoxide, used as oxidizing agent in this procedure, is an easily accessible and low cost reagent, that generates as only byproduct dimethyl sulfide, that is a volatile compound that can therefore be easily removed from the reaction media allowing a straightforward isolation of the synthesized aldehyde or ketone without the use of column chromatography.
Main advantages of its use
This is an efficient method for the synthesis of aldehydes and ketones from diols, that uses an easily accessible and environmentally friendly oxidant. Moreover, the reaction is carried out in an open vessel (there is no need of using inert atmosphere) and without the use of organic solvents (economic and environmental advantages) and the aldehydes and ketones are isolated with analytical purity without the need of column chromatography.
Specifications
The present invention relates to the use of dimethyl sulfoxide as oxidizing agent for the oxidative cleavage of 1,2-diols to carbonyl-type compounds including an aldehyde or ketone functional group, in the presence of a molibdenum (VI) catalyst, in an organic solvent or in a solvent free media, under atmospheric pressure and a temperature of 100-180 ºC or, alternatively, by irradiation in a monomode microwave oven at a maximun power of 300 W and a temperature of 120-180 ºC.
Applications
Synthesis of compounds containing an aldehyde or ketone in its structure, which are highly versatile synthetic intermediates. Therefore, applications in pharmaceutical and agrochemical industries. Manufacture of enamels in the Cosmetic Industry. In the Food Industry, as an intermediate product to give smell and flavor to food. Plastic industry, resins, paints, solvents. Explosives manufacturers.
Intellectual property status
Protected by patent P201301117
Current development status
Laboratory tested procedure.
Desired business relationship
Commercial Agreement, License Agreement, Technical Cooperation: further development; Technical Cooperation: testing new applications; Technical Cooperation: adaptation to specific needs.
The aim of the The Technology Transfer Office (TTO) of the Univesidad de Burgos is to promote Innovation technology through the reseach results transfer and the conexions between the University and the new needs and requirements of the society - we are the link between the University and the Industry. Contact person: José Manuel López (jmllopez@ubu.es)
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