Conversion Of Acetophenone Research Articles

A Novel Chiral Auxiliary for Enantioselective Synthesis of Tertiary Alcohol

The use of 1-menthyl ester of 1,3-dithiane-2-carboxylic acid as a chiral auxilary for the conversion of acetophenone, propiophenone and butyrophenone to the corresponding optically active tertiary alcohols 2-phenylhexan-2-ol, 3-phenylheptan-3-ol and 4-phenyloctan-4-ol, has been demonstrated.

Reactions of acetophenone with alcohols over oxide catalysts: Alkylation of ketones by alcohols

As part of a study of hydrogen transfer reactions over alumina, the reactions of acetophenone with methanol over η-alumina at 300–500 °C were studied. In addition to styrene arising from reductive dehydration, products arising from methylation (propiophenone, β-methylstyrene) were also observed. At higher conversion, secondary reactions like dealkylation of higher ketones and alkylation, dealkylation, and hydrogenation of olefins were also observed. Reactions have also been carried out with modified alumina (fluorided and Na +-doped) catalysts, HY-zeolite, phosphotungstic acid, and silicotungstic acid to study the effect of acidity on the selectivity for these reactions. Reactions of methanol with aralkyl ketones and with olefins were also studied. Acetophenone conversion was found to increase with increasing catalyst basicity while the selectivity for reductive dehydration decreased. Conclusions have also been drawn, on the basis of these studies, regarding the nature of the active catalytic sites responsible for the different reactions and mechanisms have been proposed for the surface reactions.

Semidiones—XVII : Formation of semidione radical anions from ketones and reducing agents with and without involvement of solvent

Mechanisms for the conversion of acetophenone (or benzaldehyde) to 1-phenylpropane-1,2-semidione (or phenylglyoxal radical anions) by electrolytic reduction in dimethylformamide are considered. The intermediate C 6H 5C(O −)(CH 3)CH(O −)X with X = (CH 3) 2N is implicated. The free α-hydroxy aldehyde is apparently not a precursor of the semidione. Other examples of this rearrangement with X = alkoxy groups are suggested. 2,2,4,4-Tetramethylcyclobutanone ketyl at −50° rapidly decomposes to yield 3,3,5,5-tetramethylcyclopentane-1,2-semidione in tetrahydrofuran solution. This novel carbonylation reaction is presumed to involve carbon monoxide reacting with the ketyl, or K +[CO] − reacting with the ketone. Decomposition of ketyls to yield semidiones in tetrahydrofuran solution apparently occurs only in the case of highly strained ketones.