Chakravarti, Duhkhaharan published the artcileSynthesis of coumarins from ¦Ï-hydroxyaryl alkyl ketones. IV. Formation of ¦Ï-coumaric acids from ¦Ï-hydroxy aldehydes, Computed Properties of 16909-09-4, the publication is Journal of the Indian Chemical Society (1943), 338-40, database is CAplus.
cf. C. A. 34, 6252.7. Reformatski¨« reactions of some 2-methoxybenzaldehydes gave HO esters which on dehydration and hydrolysis yielded trans-¦Ï-coumaric acids. It was shown that 2-MeO aldehydes, always lead to trans-¦Ï-methoxycinnamic acids by Perkin’s reaction, by malonic acid condensation, and by the method of Chakravarti and Majumdar (Reformatski¨«) (cf. C. A. 34, 2348.9). A mixture of 8 g. 5,2-Me(MeO)C6H3CHO (I), 13.4 g. BrCH2CO2Et (II), 5.5 g. Zn wool and 75 cc. anhydrous benzene was heated at 100¡ã for 2.5 h. and poured into ice-cold dilute H2SO4. After washing and drying, the benzene layer was distilled, yielding 5.5 g. of Et ¦Â-hydroxy-¦Â-(2-methoxy-5-methylphenyl)propionate, b12 200¡ã, which was converted by treating with 3 g. SOCl2 and 3 g. pyridine in 100 cc. anhydrous Et2O into 3.8 g. Et 2-methoxy-5-methyl-trans-cinnamate (III), b7 165¡ã. Hydrolysis of III with alc. KOH gave the free trans acid (IV), m. 145-6¡ã, which was identical with the compound obtained in good yield by heating 1 g. I with 2 g. Ac2O and 8 g. fused AcONa at 180¡ã for 10 h., extracting with alkali and acidifying with HCl. Similarly I was converted by Reformatski¨«’s reaction with Zn and MeCHBrCO2Et (V) to the corresponding HO ester which was dehydrated with SOCl2 and pyridine to Et ¦Á-methyl-2-methoxy-5-methylcinnamate (VI), b5 160¡ã. Alc. KOH hydrolysis of VI gave the trans acid, m. 109-10¡ã, identical with the acid obtained by heating I with EtCO2Na and (EtCO)2O. By the same series of reactions the following compounds were prepared: Et 2,4-dimethoxycinnamate, brown viscous liquid, b6 160¡ã (trans acid (VII), m. 184¡ã); Et ¦Á-methyl-2,4-dimethoxycinnamate, viscous brown liquid, b6 200¡ã (trans acid (VIII), m. 130¡ã); Et ¦Â-(2-methoxy-1-naphthyl)acrylate, b4 210-2¡ã; (free acid (IX), m. 153-4¡ã); Et ¦Á-methyl-¦Â-(2-methoxy-1-naphthyl)acrylate, viscous brown liquid, b5, 220-5¡ã (free acid (X), m. 138-9¡ã). VII, VIII, IX, and X were also prepared by Perkin’s reaction and were compared with those compounds prepared above by mixed m. ps. In addition, condensation of 2,4-(MeO)2C6H3CHO with malonic acid in the presence of piperidine also yielded the trans acid (VII). III or IV, heated with HI (d. 1.7) at 140¡ã for 2 h., yielded only a sticky precipitate which could not be crystallized No ring closure was effected.
Journal of the Indian Chemical Society published new progress about 16909-09-4. 16909-09-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ether, name is (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, and the molecular formula is C11H12O4, Computed Properties of 16909-09-4.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia