Production of 2-substituted-1,3-dioxolanes from 1,3-dioxolane an

Details Production of 2-substituted-1,3-dioxolanes from 1,3-dioxolane an Production of 2-substituted-1,3-dioxolanes from 1,3-dioxolane an

1984-12-19

1986-12-09

Love, Ethel G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D31700

Patent

active

046281088

ABSTRACT:
It has been surprisingly discovered in accordance with the present invention that when 1,3-dioxolane is reacted with formaldehyde in the presence of an organic peroxide and an ionizable, at least sparingly soluble metal salt, the reaction preferentially involves an addition of the formaldehyde to the 2-methylene group of the 1,3-dioxolane with only minor reaction with the 4-methylene and 5-methylene groups of the 1,3-dioxolane whereby the reaction product that is formed contains significant quantities of 2-hydroxyalkyl-1,3-dioxolanes. 2-Hydroxyalkyl-1,3-dioxolanes are hydrolyzed with comparative ease to ethylene glycol and the corresponding glycol aldehyde (CHO--CH.sub.2 --OH). The glycol aldehyde in turn can be catalytically hydrogenated to form additional quantities of ethylene glycol.

REFERENCES:
patent: 2140938 (1938-12-01), McNamee et al.
patent: 2862978 (1958-12-01), Skanner et al.
patent: 4200765 (1980-04-01), Goetz
patent: 4337371 (1982-06-01), Kollar
"A Free-Radical Reaction of Primary and Secondary Alcohols with Formaldehyde", O. Yano, J. Org. Chem. 30, 2429 (1965).
"Oxygen Promoted Addition of 1,3-Dioxolane to Electron Deficient Alkenes", Watanabe et al., Bull Chem Soc Jpn 56, 1428-30, (1983), vol. 56, No. 5.

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