Favorskii Rearrangement
Favorskii rearrangement
[fa′vȯr·skē ‚rē·ə′rānj·mənt]Favorskii Rearrangement
a reaction for the synthesis of tertiary acetylenic alcohols through the condensation of hydrocarbons of the acetylene series with ketones in the presence of anhydrous, powdered potassium hydroxide. For example, acetylene reacts with acetone to form methyl butynol (2-methyl-3-butyn-2-ol):
HC≡CH + CH3COCH3 → (CH3)2C(OH)C≡CH
The reaction occurs in ether, benzene, and other organic solvents on cooling and mixing. Great practical value is attached to, for example, dimethylvinylethynyl carbinol:
(CH3)2C(OH)C≡C—CH=CH2
which is synthesized from vinylacetylene and acetone; copolymerization of dimethylvinylethynyl carbinol with methyl metha-crylate and/or butyl methacrylate yields carbinol resins, which are used in the manufacture of varnishes and glues. The reaction was discovered by A. E. Favorskii in 1900.