Dimethylethynyl carbinol

This is an example of an acetylenic alcohol. It is prepared from acetone by the following series of reactions  

Methylethylethynyl carbinol. Use 144 g. (179 ml.) of dry methyl ethyl ketone, and other quantities as above. The yield is 60 g., b.p. 119-123°. 

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Pour the reaction mixture cautiously into 400 g. of crushed ice and acidify it in the cold by the addition of a solution prepared by adding 55 ml. of concentrated sulphuric acid to 150 ml. of water and then coohng to 0°. Separate the ether layer and extract the aqueous layer twice with 50 ml. portions of ether. Dry the combined ethereal solutions over 50 g. of anhydrous potassium carbonate and distil the filtered solution thror h a Widmer column (Figs. II, 17, 1 and II, 24, 4). Collect separately the fraction boihng up to 103°, and the dimethylethynyl carbinol at 103-107° Discard the high boiling point material. Dry the fraction of low boihng point with anhydrous potassium carbonate and redistil. The total 3 ield is 75 g. 

Dimethyl-1 3-butadiene Dimethylethynyl carbinol 10-Undecynoic acid. ... 

Dimethylethynyl carbinol has usually been prepared by the addition of acetylene to the sodium derivative of acetone,3 4 5 6 7>8 but potassium metal9 and sodium ethoxide10 have also been used. The above method is based upon that described by Sung Wou-seng.3 A more recent method uses potassium hydroxide, calcium carbide, and acetone.11... 

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