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Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is an organic compound with the formula C 17 H 14 O. It is a pale-yellow solid insoluble in water, but soluble in ethanol. It is a pale-yellow solid insoluble in water, but soluble in ethanol.
[1] [2] [3] An example is the synthesis of dibenzylideneacetone ((1E, 4E)-1,5-diphenylpenta-1,4-dien-3-one). [ 4 ] Quantitative yields in Claisen–Schmidt reactions have been reported in the absence of solvent using sodium hydroxide as the base and plus benzaldehydes . [ 5 ]
Dibenzyl ketone, or 1,3-diphenylacetone, is an organic compound composed of two benzyl groups attached to a central carbonyl group. This results in the central carbonyl carbon atom being electrophilic and the two adjacent carbon atoms slightly nucleophilic.
The mechanism for base-catalyzed aldol condensation can be seen in the image below. A mechanism for aldol condensation in basic conditions, which occurs via enolate intermediates and E1CB elimination. The process begins when a free hydroxide (strong base) strips the highly acidic proton at the alpha carbon of the aldehyde.
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Benzylideneacetone can be efficiently prepared by the base-induced condensation of acetone and benzaldehyde: [3]. CH 3 C(O)CH 3 + C 6 H 5 CHO → C 6 H 5 CH=CHC(O)CH 3 + H 2 O. However, the benzylideneacetone formed via this reaction can undergo another Claisen-Schmidt condensation with another molecule of benzaldehyde to form dibenzylideneacetone.
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