高級脂肪酸エステルと金属ナトリウムとの反応 (第5報) : α-グリコールの合成およびその性状

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The C12C36 sym. α-glycols were prepared from acyloins by catalytic hydrogenation with Raney nickel. The properties of α-glycols were studied. Melting point of the α-glycol is higher than that of the corresponding acyloin or α-diketone and decreases with chain length. Two hydroxyl groups can be quantitatively acetylated by acetic anhydride, and reacted with 3, 5-dinitrobenzoyl chloride to give the crystalline 3, 5-dinitrobenzoate. From mp and optical rotation of fractional crystals, α-glycols obtained by catalytic hydrogenation seem to consist of meso or racemic form. In the acetic acidical solution α-glycols are quantitatively oxidized with periodic acid as well as ethylene glycol, and in the 99% alcoholic solution the oxidation by periodic acid is quite the same as acyloins. When heated to 200°C, these α-glycols are hard to change into ketones by dehydration. α-Glycols show the broad absorption band in the range of 2.293.01μ assigned to associated hydroxyl groups, and complicated bands of C-O stretching in the range of 810μ.
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