Acetone benzylidene

A patent of Meister, Lucius, Briining [46] depends on a similar reaction. Claisen s benzylidene-acetone (cinnamylmethyl-ketone CeHj —CH = CHCO—CH3) [47], obtained by condensation of benzaldehyde and acetone, is nitrated. A mixture of ortho and paranitro derivatives is formed, and the former yields indigotin by action of alkalies. 

Indigotin may also he obtained from ortho-amidophenylacety-lene by an analogous process. 

Gevekoht [50] obtained indigotin by action of ammonium sulphide on ortho-nitroacetophenoiie, in which the methyl group is brominated. 

From the researches of Baeyer [51] and Bloem it is shown that on brominating acetylortho-amidoacetophenone, the bromine atom enters in the methyl group. If the benzene chain is substituted brominated indigos are formed but if only the benzene chain contains bromine, indigo cannot be produced. In these reactions indoxyl appears to be formed as an intermediate product in the reaction. 

Meyer [52] prepared substituted indigo blues from the corresponding substituted isatins. This process depends on the fact that the final products of the action of dichloracetic acid on amines in which the para position is occupied are substituted isatins. The first product of the action of dichloracetic acid on paratoluidine is a paratolylimide derivative of paramethylisatin, CieHigNjO, which decomposes on boiling with acids into paratoluidine and methylisatin, C9H7NO2. 

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Various 4-, 5-, or 4,5-disubstituted 2-aryIamino thiazoles (124), R, = QH4R with R = 0-, m-, or p-Me, HO C, Cl, Br, H N, NHAc, NR2, OH, OR, or OjN, were obtained by condensing the corresponding N-arylthiourea with chloroacetone (81, 86, 423), dichloroacetone (510, 618), phenacyichloride or its p-substituted methyl, f-butyl, n-dodecyl or undecyl (653), or 2-chlorocyclohexanone (653) (Method A) or with 2-butanone (423), acetophenone or its p-substituted derivatives (399, 439), ethyl acetate (400), ethyl acetyl propionate (621), a- or 3-unsaturated ketones (691), benzylidene acetone, furfurylidene acetone, and mesityl oxide in the presence of Btj or Ij as condensing agent (Method B) (Table 11-17). 

Benzylidene acetone, C Hg. CH CH. COCH, is a crystalline body melting at 42°, having an intense floral odour. It restilts from the condensation of benzaldehyde and acetone under the influence of caustic soda. It has the following characters —... 

This behaviour is shown in the voltammetry of 68 which leads under suitable conditions to the formation of benzylidene acetone at the cathodic interface. The latter structure exhibits a reversible step, i.e., formation at — 1.25 V of a fairly stable anion radical. 

The Michael reaction of benzylidene acetophenone and benzylidene acetone with ethyl acetoacetate, nitromethane, and acetylacetone was studied by Musaliar and co-workers in the presence of a cetyltrimethy-lammonium bromide-containing aqueous micellar medium.50 The Michael reaction of various nitro alkanes with electrophilic alkenes is performed in NaOH (0.025-0.1 M) in the presence of cetyltrimethylam-monium chloride (CTACI) without any organic solvent (Eq. 10.23).51... 

RuCl(Cp)(pta)2] 1-decene cyclohexene styrene benzylidene-acetone... 

An enormous variety of olefinic types have been found to undergo such solid-state (2 + 2) photocyclodimerizations. These include cinnamic acids (128,132) derivatives of cinnamic acids such as esters (133) and amides (134) styrene derivatives (135) stilbenes (136) aliphatic mono- (137), di- (138), and triene (139) dicarboxylic acids and derivatives 1,4-diarylbutadienes (140) and their vinylogs (141), benzylidene acetones (142) and benzylidene acetophenones (143) ... 

The influence of benzylidene acetone on the electrodeposition mechanism of Zn-Co alloy was investigated [436]. A relationship between corrosion resistance, microstructure, and cobalt content in Zn-Co alloys was investigated [437] using X-ray photoelectron spectroscopy (XPS) and Auger spectroscopy [438]. The role of vitreous carbon, copper, and nickel substrates in Zn-Co deposition from chloride bath was analyzed [439]. 

C10H12O, Mr 148.20, pioi.3kPa 233-234°C, df- 0.9849, Up 1.5110, has been identified as a volatile component of cocoa. Benzylacetone is a sweet-flowery smelling liquid, which can be prepared by selective hydrogenation of benzylidene acetone (from benzaldehyde and acetone). It is used in soap perfumes. 

This compound is also of the coumarin family. The fonnula is 3-(alpha-acetonylbenzyl)-4-hydroxycoumarin. In addition to use in anticoagulant therapy in medicine, the compound also has been used as a major ingredient in rodenhcides, where the objective is to induce bleeding and, when used in heavy doses, is thus lethal. The compound can be prepared by the condensation of benzylidene-acetone and 4-hydroxycoumann. 

Using benzaldeliyde and acetone, he obtained mono- and di-benzylidene acetone. 

The conjugation of a double bond with a carbonyl group, C O, such as in an aldehyde, can have the serious adverse effect of greatly increasing the likelihood of the material being a severe skin irritant or sensitizer. Examples of this type of influence occur in citral, cinnamic aldehyde, and trans-2 hexenal, as well as in methyl heptine carbonate which has a conjugated triple bond. Benzylidene acetone, which is closely related in structure to cinnamic aldehyde, can no longer be used as a perfumery material for this reason, and the level at which other potential sensitizers can be used in perfume formulations is restricted (see pp. 183-185). 

Ac = Acetyl acac = Acetylacetonate bda = Benzylidene-acetone BINOL = l,l -bi-2-naphthol Bn = Benzyl brsm = Yield based on recovered starting material Bu = Bntyl CAN = Ceric anunonium nitrate CBS = Corey/Bakshi/Shibata catalyst [(+) or (—)-(S)-2-methyl-oxazaborolidine] COD = Cyclo-l,5-octadiene COT = Cyclooctatetraene Cp = Cyclopentadienyl Cp = Penta-methylcyclopentadienyl Cy = Cyclohexyl DCC = Dicy-clohexylcarbodiimde DMF = Ai,A-dimethylformainide DMPU = l,3-dunethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidin-one DMSO = Dimethylsnlfoxide dppe = Diphenylphosp-hinoethane dr = Diastereomer ratio dppm = Diphenylphos-phinomethane E = Electrophile ee = Enantiomeric excess EHMO = Extended htickel molecular orbital Et =... 

Preparation of Cinnamic Acid from Benzylidene Acetone... 

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