Desoxy benzoin

Triphenylethylene has been prepared by the reaction of phenylmagnesium bromide with benzyl benzoate, with desoxy-benzoin, or with ethyl pheaniylacetate, and by the reaction of diphenylketene-quinoline with benzaldehyde. The above procedure is an adaptation of that described by Hell and Wiegandt. ... 

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-... 

Tetraphenylcyclopentadienone has been prepared by the action of phenylmagnesium bromide on benzaldiphenylmaleide,1 and by reduction, dehydration, and oxidation of the methylene-desoxybenzoin obtained by condensing formaldehyde with desoxy-benzoin.2 The present procedure is essentially that of Dilthey.3... 

Isoflavanones.1 A synthesis of these products from a poly hydroxy desoxy-benzoin such as 2 involves conversion of the nonhydrogen-bonded hydroxyl group to the protected ether by reaction with 1 and K2C03 in acetone at 25°. Further reaction with 1 at 60-70° gives an a-hydroxymethyl ketone 3 in 85-95% yield. This product cyclizes to the isoflavanone 4 in the presence of Na2C03. The final step involves deprotection of the ethoxymethyl group to give 5 (92-94% yield). 

Ci7H BtOj /S-[5-Brom.2-aoetoxy-phenyl]-propiophenon 8,180. ms-Broin.6-aoeto -3.methyl.desoxy benzoin 8 II 208. 

Boizophra( . [4 aootozy antt] 16 IT 238. ms-[44 >zy>phenyUmmcmet hyl] desoxy benzoin 13II241. 

C HaClallaO, Verbmdung CagH OlaN.O, ans ms- [3-Chior-N-benz< l-anuino]-desoxy> benzoin-[3-ohlor-anil] 14 1 397. 

Preparation by reaction of dimethyl sulfate with 2,4-di-hydroxy-5-(diphenyl-methyl)desoxy-benzoin in the presence of potassium carbonate in refluxing acetone for 3 h (93%) [5274]. 

Preparation by catalytic hydrogenation of 2,4-dihydroxy-4 -(benzyloxy)desoxy-benzoin [5443]. 

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