Lutz, Robert E. published the artcileThe cis- and trans-3-aroyl-2- and 3-methylacrylic acids and 3-aroyl-2-methylenepropionic acids, Formula: C11H10O3, the publication is Journal of the American Chemical Society (1953), 5039-44, database is CAplus.
Ultraviolet absorption studies on the cis-3-aroyl-2- and 3-methylacrylic acids and related compounds showed that the cis compounds in solution are cyclic but are open-chain in the form of anions. The cis-3-benzoyl-2- and 3-methyl compounds and both 3-aroyl-2-methylenepropionic acids have been made, resp., from citraconic (I) and itaconic anhydride (II) by Friedel-Crafts reactions. The trans isomers are the stable forms; the cis isomers are labile; and the 3-aroyl-2-methylenepropionic acids also are labile and the least stable of the 3 types. Interconversions of the various isomers are described. II (50 g.) added during 1 hr. with stirring to 140 g. AlCl3, 80 cc. dry C6H6, and 150 cc. dry CS2 at 45°, the mixture stirred 1 hr. at 50-5° and 10 hrs. at room temperature, hydrolyzed with ice and concentrated HCl, filtered, and the colorless crystalline material (59 g.), m. 138-40°, triturated with 500 cc. boiling C6H6 left 40 g. BzCH2C(:CH2)CO2H (III), m. 148-52°. The EtOH filtrate from the III gave on cooling 12.5 g. material, m. 125-8°, which recrystallized from C6H6 (m. 130-1°) and fractionally recrystallized from 60% EtOH, yielded 7 g. III and 4 g. (5%) of a new isomer, m. 146-7°, which appeared to be a nuclear cyclization product and was oxidized by KMnO4 to o-C6H4(CO2H)2. The alc. filtrate and the C6H6-CS2 filtrate from the crude III gave an addnl. 6.7 g. III (total yield 63%). III is readily soluble in aqueous Na2CO3, very slowly soluble in aqueous NaHCO3, and decolorizes KMnO4 in Me2CO. PhBr and II gave similarly 91% p-BrC6H4COCH2C(:CH2)CO2H (IV). I (50 g.) added with stirring to 130 g. AlCl3, 100 cc. C6H6, and 150 cc. CS2 during 1 hr. at 50°, the mixture heated 0.5 hr., stirred overnight, and hydrolyzed with ice and HCl, the organic layer evaporated in an air stream, the residue extracted with 400 cc. 10% aqueous Na2CO3, the extract washed with C6H6, acidified with HCl, extracted with C6H6, and the extract concentrated to 100 cc., and cooled gave 39 g. (46%) cis-BzCMe: CHCO2H (V), m. 65-75° (recrystallized, it m. 79-80°). The filtrate from the crude V diluted with petr. ether and cooled gave 12 g. (14%) cis-BzCH:CMeCO2H (VI), m. 70-80° (recrystallized from CCl4, it m. 92-3°). V and VI are soluble in hot H2O and cold aqueous NaHCO3, and decolorize acidic KMnO4. III (1 g.) and 5 cc. Et3N in 15 cc. Et2O let stand 24 hrs., the mixture evaporated, extracted with dilute HCl, and the resulting product recrystallized from EtOH gave 0.85 g. trans-isomer (VII) of VI, m. 109-10°. The isomerization of III also occurred slowly in NaOH solution, and in 10 min. by heating at 175°. The oily Me ester of trans-BzCMe: CHCO2H (VIII) was prepared by a previously described method (C.A. 27, 2426), immediately hydrolyzed during 2 hrs. at room temperature, the mixture washed with Et2O, acidified, extracted with Et2O, the extract evaporated, and the residue crystallized from C6H6CCl4 to give 41% VIII, m. 90-4° (recrystallized from aqueous EtOH, it m. 102-3°). III hydrogenated over PtO2 yielded 81% BzCH2CHMeCO2H (IX), m. 138-40°; semicarbazone, m. 220-3°. The hydrogenation of IV over Raney Ni at atm. pressure yielded 88% p-BrC6H4COCH2CHMeCO2H (X), m. 120-2°. The reduction with Zn and AcOH gave high-melting and presumably dimeric substances, m. 204-12°, from III, and m. above 350° from IV, which were not investigated further. VI and VII heated 10 min. with Zn and AcOH on the steam bath gave IX, m. 138-40°, in 79 and 81% yield, resp. The similar reduction of VII and VIII during 20 min. gave MeCHBzCH2CO2H, m. 59-60°, in 63 and 71% yield, resp.; semicarbazone, m. 177-8°. III, VI, and VII (1 g. each) refluxed 4 hrs. with 6-8 g. Ba(OH)2, and the mixture steam-distilled gave in each case a high yield of PhAc, identified as the semicarbazone, m. 197-8°. V and VIII hydrolyzed similarly yielded 71 and 50% PhCOEt, resp.; semicarbazone, m. 172-3°. IV and cis-4-BrC6H4COCH:CMeCO2H (XI) gave similarly 69 and 51% p-BrC6H4Ac, m. 51-2°, resp.; oxime, m. 127-9°. The trans isomer (XII) of XI gave similarly 57% p-BrC6H4COEt, m. 46-8°; oxime, m.88-9°. The following isomerizations were carried out by the method described for the isomerization of III to VII: IV to 90% trans-p-BrC6H4COCH:CMeCO2H (XIII), m. 182-4°; XI to 70% XIII; and VI to 88% VII, m. 104-6°. VI dissolved in NaOH or aqueous NaHCO3, or heated 10 min. at 175° was also isomerized to VII. Et3N or heat failed to isomerize V. V in Et2O treated with morpholine gave an addition compound, m. 138-40°, which, when decomposed with warm 10% HCl, yielded 40% VIII, m. 100-2°. Et3N did not isomerize cis-p-BrC6H4COCMe:CHCO2H (XIV) to the trans isomer. VII (1 g.) in 50 cc. dry Et2O exposed 2 days to sunlight, the mixture evaporated, and the residue recrystallized from hot C6H6 gave 0.9 g. VI, m. 80-5° (recrystallized from C6H6, it m. 89-92°). VII in Et2O exposed to sunlight 1 week, or VI 4 days, gave 40-50% III, m. 152-4° (from aqueous EtOH). Similarly were isomerized: XI to 30% IV, m. 160-2° (from C6H6); XIII to IV; VIII to 80% V, m. 68-76° (recrystallized from CCl4, it m. 78-80°); and XII to 64% XIV, m. 130-5° (recrystallized from CCl4, it m. 138-41°). The ultraviolet absorption spectra of XIV, the cyclic Me ester of XIV, the salt of XIV, the straight-chain cis-Me ester of XIV, XII, the salt and the Me ester of XII, p-BrC6H4COCHMeCH2CO2H, XI, the salt of XI, XIII, Me ester of XIII, X, and IV are recorded.
Journal of the American Chemical Society published new progress about 15732-75-9. 15732-75-9 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ketone, name is 2-Methylene-4-oxo-4-phenylbutanoic acid, and the molecular formula is C11H10O3, Formula: C11H10O3.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia