Desoxybenzoins benzils

Benzil (Coll. Vol. i, 80) By oxidation of desoxybenzoin with selenium dioxide in acetic anhydride at 140-150°, in 90 per cent yield. Hatt, Pilgrim, and Hurran, J. Chem. Soc. 1936, 93. 

The procedure described is essentially that of Ballard and Dehn.1 Stilbene has also been prepared by reduction of desoxy-benzoin,20 benzaldehyde,23 and benzil 2o-2c by dehydrogenation of ethyl benzene,30 toluene,30- 33- 3, and bibenzyl 33-3alkaline reduction of phenylnitromethane,40 phenylnitroacetonitrile,40 and desoxybenzoin 43 by distillation of benzyl sulfone,50 benzyl sulfide,60-63 calcium cinnamate,5 cinnamic acid,5d phenyl cinna-mate,6e-6/ and diphenyl fumarate ie by dehydrohalogenation of a,a -dichlorobibenzyl60 and benzyl chloride 63 by dehalogenation of a,a,c/,a -tetrachlorobibenzyl70 and benzal chloride 73 by the coupling of cinnamic acid and phenyldiazonium chloride 8 by de-... 

Nickel prepared by reduction of nickel chloride with sodium borohydride was used for desulfurization of diethyl mercaptole of benzil. Partial desulfurization using 2 mol of nickel per mol of the mercaptole gave 71% yield of ethylthiodesoxybenzoin while treatment with a 10-fold molar excess of nickel over the mercaptole gave 61% yield of desoxybenzoin (benzyl phenyl ketone) 937. ... 

Desoxybenzoin has been prepared by treatment of bromo-stilbene with water in a sealed tube at 180-190° 1 by the reduction of benzoin 2 by the reduction of benzil 3 by the action of zinc and alcoholic hydrogen chloride on chlorobenzil 4 by the action of benzene on phenylacetic acid in the presence of phosphorus pentoxide 5 and by the action of benzene on phenylacetyl chloride in the presence of aluminum chloride.6... 

Corey and Schaefer studied the kinetics of the oxidation of desoxybenzoin to benzil and suggested a mechanism for the reaction. They also developed an efficient synthesis of a-keto esters involving oxidation of an a-bromoketone in an anhydrous solvent, as illustrated by a procedure for the preparation of ethyl benzoyl formate. o OO OO... 

Oxidation of benzoins to benzils Benzoins (1) are oxidized to benzils(2) in high yield by catalytic amounts of this lanthanide nitrate and 1 eq. of HCl in aqueous glyme. Benzil can also be obtained from desoxybenzoin and diphenyl-acetylene under these conditions. This oxidation has recently been reported with... 

Benzil crystallizes from alcohol in yellow needles which melt at 95°. It takes part in many reactions which are characteristic of ketones. It may be reduced to desoxybenzoin,... 

Benzoin is oxidized by nitric acid to benzil, CeHs.CO.CO.CeHs. It is reduced by zinc and hydrochloric acid in alcoholic solution to desoxybenzoin, C6H5.CO.CH2.C6H5, by sodium amalgam to hydrobenzoin, C6H5.CHOH.CHOH.C6H5, and by hydriodic acid to dibenzyl, CeH5.CH2.CH2.C6H5. 

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