Org. Synth. 1931, 11, 52
DOI: 10.15227/orgsyn.011.0052
dl-GLYCERALDEHYDE ETHYL ACETAL
    Submitted by E. J. Witzemann, Wm. Lloyd Evans, Henry Hass, and E. F. Schroeder.
    Checked by Frank C. Whitmore and Harry T. Neher.
1. Procedure
In a 
3-l. open flask, equipped with a 
mechanical stirrer and a 
thermometer and cooled in an 
ice bath, is placed a suspension of 
65 g. (0.5 mole) of acrolein acetal (p. 17) in 600 cc. of water. The suspension is cooled to 5° 
(Note 1), and a solution of 
80 g. (0.5 mole) of potassium permanganate in 1.5 l. of water is added, with stirring, at the rate of about 25 cc. per minute. The temperature is kept as near 5° as possible during the addition. Soon after the stirring is stopped, the mixture sets to a gel 
(Note 2). After standing for two hours, the mixture is heated for one hour on the 
steam bath and then filtered by suction on a 
30-cm. Büchner funnel. The residual 
manganese dioxide is pressed thoroughly and washed with 150 cc. of cold water. The filtrate (about 2.3 l.) is kept cool and treated with 
1.2 kg. of freshly dehydrated commercial potassium carbonate. The layers are separated and the water layer is extracted with four 
100-cc. portions of ether. The 
ether extracts are added to the crude acetal layer, and the mixture, which may consist of two layers 
(Note 3), is dried over 
10 g. of potassium carbonate. After removal of the 
ether, the residue is distilled under reduced pressure. The yield of product boiling at 
120–121°/8 mm. is 
55 g. (
67 per cent of the theoretical amount).
 
2. Notes
1.
    The oxidation is very sensitive to changes in temperature. The best results are obtained at 5°; a slight variation causes a marked decrease in the yield.
2.
    If the mixture does not set to a gel, the yield is likely to be poor. This is usually due to poor temperature control.
3.
    Sometimes two layers appear at first, but these disappear when the 
potassium carbonate is added.
 
3. Discussion
dl-Glyceraldehyde acetal has been prepared by heating 
hydroxychloropropionaldehyde acetal with 
potassium carbonate solution;
1 by treating 
glyceraldehyde with alcoholic 
hydrogen chloride;
2 and by oxidation of 
acrolein acetal with 
potassium permanganate.
3 
This preparation is referenced from:
Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
potassium carbonate (584-08-7)
hydrogen chloride (7647-01-0)
ether (60-29-7)
potassium permanganate (7722-64-7)
manganese dioxide (1313-13-9)
Acrolein acetal
glyceraldehyde (56-82-6)
hydroxychloropropionaldehyde acetal
DL-Glyceraldehyde acetal
dl-GLYCERALDEHYDE ETHYL ACETAL
 
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