3. Other Methods of Preparation
Phenylacetylene has been prepared by the elimination of carbon dioxide from phenylpropiolic acid by means of phenol[1] or aniline[2] or by heating with barium hydroxide;[3] from styrene dibromide, by heating with potassium hydroxide in alcohol;[4] by heating b-bromo or chloro styrene with sodium ethylate or potassium hydroxide in alcohol;[5] by passing the vapors of a-dichloroethylbenzene over hot soda lime;[6] by the action of alcoholic potassium hydroxide on dibenzal-acetone tetra-bromide;[1b] by the action of aqueous potassium hydroxide on phenyl propargylaldehyde;[2b] by the action of molten potassium hydroxide on b-bromo-styrene.[3b]
[1] Ber. 20, 3081 (1887).
[2] Rec. trav. chim. 16, 157 (1896).
[3] Arm. 221, 70 (1883).
[4] Ann. 154, 155 (1870); 235, 13 (1886); Bull. soc. chim. 35, 55 (1881); (3) 25, 309 (1901).
[5] Ann. 308, 265 (1899); 342, 220 (1905).
[6] Jahresb. 1876, 308; Gazz. chim. ital. 22 (2), 67 (1892); Bull. soc. chim. (3) 25, 309 (1901).
[1b] Ber. 39, 4146 (1900).
[2b] Ber. 31, 1023 (1898).