Here are some references for the first reaction
The product is this correct?
3-methyl-4-phenyl-3-Buten-2-one
Preparation of 3-methyl-3-penten-2-one and its analogs.
Pishch. Prom-st. (Moscow) (1990), (10), 44-5.
Journal written in Russian.
Abstract
MeCOEt condensed with RCHO (R = Me, Et, Pr, Me2CH, MeOC6H4, PhCH:CH, Ph) in the presence of H2SO4 at 60-65° to give 40-79% RCH:CMeCOMe. Analogous reaction of R1CH2COR2 [R1R2 = (CH2)3, (CH2)10; R1 = H, R2 = Ph, CH2CHMe2; R1 = C5H11, R2 = Me] with MeCHO (from paraldehyde) gave 8.6-38% MeCH:CR1COR2.
Aldol condensation of butanone with various aldehydes.
Sasaki, Kazuhiro. Kobayashi Perfum. Co., Ichikawa, Japan.
Nippon Kagaku Zasshi (1968), 89(
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, 797-804.
Journal written in Japanese.
Abstract
Condensation of MeCOEt (I) with various aldehydes was investigated to find the effect of conditions on the ratio of RCH:CHCOEt (II) and RCH:CMeAc (III). Citral and I, in the presence of alkali hydroxide or NaOEt, gave products contg. >86.8% II, whereas MeOH-KOH yielded products contg. III as a main product. Citronella (IV) and I gave similar results except that Me2C:CHCH2CH2CHMeCH2CH(OMe)CH2COEt was formed using MeOH-KOH and Me2C:CHCH2CH2CH(Me)CH2CH(OH)CHMeAc was obtained with EtONa. The results indicate that aldol corresponding to II is more readily dehydrated than that corresponding to III. Condensation of IV with Me2CO in the presence of MeOH-KOH gave a mixt. of Me2C:CHCH2CH2CHMeCH2CH:CHAc and Me2C:CHCH2CH2CHMeCH2CH(OMe)CH2Ac. Similar reaction of I with Et2CO gave Me2C:-CHCH2CH2CHMeCH2CH:CMeCOEt, b0.55 101-7°. Condensation of I with BzH, PhCH:CHCHO (V) and furfural (VI) showed that the ratio II-III is also dependent on the type of aldehyde. III is favored when KOH-MeOH is used with BzH and V, compared with the results with aq. NaOH, but the difference is much greater with BzH. BzH and VI always favor formation of II. PhCH:CHCH:CHCOEt, m. 55-6°, was prepd. by a modified Wittig reaction; semicarbazone m. 200-1°; phenylhydrazone m. 89-90°. 4-(2-Furyl)-3-methyl-3-buten-2-one, b10 114-15°, and 5-(2-furyl)-4-penten-3-one, b13 122-4°, were also prepd. by this method. Orientation of condensation was postulated to be regulated by the steric requirement. s-Cis and s-trans conformations of some of the unsatd. ketones were detected by ir spectra.
A study of the reaction of butanone with benzaldehyde and p-nitrobenzaldehyde.
Jung, Duksang. Cheju Univ., Cheju, S. Korea.
Nonmunjip - Cheju Taehak (1982), 14 27-31.
Journal written in Korean.
Abstract
In alk. medium, the reaction of p-O2NC6H4CHO and MeCOEt gave three hydroxy ketones, indicating that both Me and CH2 positions were attacked to a comparable extent. Dehydration of the intermediate hydroxy ketones is a slow step. In acid medium, however, the addn. step of the reaction was selective, giving only 1 isomer. Similarly, in alk. medium, PhCH(OH)CH2COEt (I) and PhCH(OH)CHMeCOMe (II), hydroxy ketone intermediates from the reaction between BzH and MeCOEt, gave PhCH:CHCOEt (III). Treating I and II with acid gave III and PhCH:CMeCOMe, resp., with no evidence of rearrangement.
These journal articles detail its synth also.
Double Michael addition reactions of some new 1,5-diaryl-2-alkyl-1,4-pentadien-3-ones: Part II.
Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. (2001), 40B(
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, 667-673.
RuCl3 catalyzes aldol condensations of aldehydes and ketones.
Tetrahedron (1998), 54(32), 9475-9480.
Synthesis of isoquinoline-1,3-dicarboxylic acid.
Chin. Chem. Lett. (1999), 10(11), 907-910.
(in english)
Here is the baseic addition
Kinetics of condensation of benzaldehyde and its derivatives with acetone and methyl ethyl ketone catalyzed by aluminum oxide.
Collect. Czech. Chem. Commun. (1980), 45(6), 1812-19.
Journal written in English.
Abstract
The pseudo-1st-order aldol condensation kinetics of RC6H4CHO (R = H, 4-Me, 3-MeO, 4-MeO, 3-Cl,4-Cl) with excess Me2CO over Al2O3 at 60-160° and the pos. r indicated that the addn. step, to give hydroxy ketone, is rate detg. r Decreases with increasing temp.; the isokinetic temp. is 449.8K. At 60-90° the retroaldol reaction of PhCH(OH)CH2Ac is minor and the dehydration to PhCH:CHAc is major; the proportion of dehydration-retroaldol reaction increases with increasing solvent polarity and decreases with increasing temp. The condensation of PhCHO with MeCOEt at 90-160° gives mostly PhCH:CHCOEt in a reaction catalyzed by the basic sites on Al2O3; the minor product, PhCH:CMeAc, formation is catalyzed by the acidic Al2O3 sites.
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