The hydrogenation of 1-furyl-2-oxa-4-butanol in a flow system at normal pressure on a Pd-C-catalyst at 180° and 280°, and also on Raney Cu-Al- and Ni-Al-catalysts at 240° were studied.
At 180° on a Pd-C-catalyst, 1-furyl-2-oxa-4-butanol smoothly hydrogenates to 1-tetrahydrofuryl-2-oxa-4-butanol. Raising the temperature to 280° makes possible the hydrogenolysis of the ether bond in the side chain.
The Cu-Al-catalyst possesses the property of most effectively causing hydrogenolysis of the side ether bond (50%), whereas hydrogenolysis of the furan ring with subsequent cyclodehydration leading to propyldioxane is observed to a lesser degree (20%).
“Conjugated” hydrogenolysis of the furan ring occurs on the Raney Ni-Al-catalyst leading to the formation of methyl-, ethyl-, and propyldioxanes from 1-furyl-2-oxa-4-butanol in yields of 18, 10, and 14%, respectively.
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Shuikin, N.I., Bel'skii, I.F. & Khar'kov, S.N. Catalytic transformations of 1-furyl-2-oxa-4-butanol. Russ Chem Bull 16, 2034–2036 (1967). https://doi.org/10.1007/BF00909615