Nerdel, Friedrich; John, Ute published an article in 1956, the title of the article was Hydratropic acids. V. Optically active m- and p-substituted homohydratropic acids.Product Details of 456-12-2 And the article contains the following content:
cf. C.A. 49, 13938c. Methylation of p-O2NC6H4CH2CHMeCO2H (I) with CH2N2 in EtOH yields 93% Me ester, b0.002 90°, m. 57° (amide, needles, m. 116°). I (60 g.) in 100 cc. (Me2CH)2O with 50 g. (+)-bornylamine (II) in 50 cc. (Me2CH)2O yields almost 100% II salt, m. 161-3°, [α]D20 11°, which, on fractional crystallization from C6H6 gives 38 g. (-)-salt, m. 168-9°, [α]D20 -3.5°; decomposition of the latter yields (-)-I, needles, m. 107°, [α]D20 -32.4° (EtOH) [Me ester, sirup, [α]D20 -49.1° (EtOH); amide, m. 112-13°, [α]D20 -60.5° (EtOH)]. m-O2NC6H4CH2CHMeCO2Me b0.05 100° (amide, small needles, m. 113°). m-O2NC6H4CH2CHMeCO2H (III) (95 g.) with 65 g. II gives the II salt, m. 144-6° [α]D20 13.4°, which, fractionally crystallized from C6H6, yields 50 g. II salt of (-)-III, m. 159-60°, [α]D20 0°; free (-)-III, m. 69-70°, [α]D20 -24°; quinine salt, m. 83-5°, does not change the rotation; Me ester, b0.001 85°, [α]D20 -40.1°; amide, needles, m. 135°, [α]D20 -61.6°. Reduction of 6.3 g. I in 75 cc. EtOH 20 min. with 0.2 g. PtO2 yields the p-NH2 acid (IV).HCl, pale yellow needles, m. 191° (decomposition); free IV, needles, m. 126°. Reduction of (-)-I in the same way yields (-)-IV, m. 191° (decomposition), [α]D20 -46° (H2O); N-Ac derivative of (-)-IV, prisms, m. 129°, [α]D20 -22.4° (EtOH). Reduction of III with PtO2 in EtOH gives m-H2NC6H4CH2CHMeCO2H (V), m. 99°. Hydrogenation of m-O2NC6H4CH:CMeCO2H gives, after 3 moles H are absorbed, m-H2NC6H4CH:CMeCO2H, m. 137°; further hydrogenation yields V. (-)-V, m. 94°, [α]D20 -14.3°; HCl salt, m. 136°, [α]D20 -42.8°. N-Ac derivative of V, prisms, m. 137°; N-Ac derivative of (-)-V, prisms, m. 123°, [α]D20 -21° (EtOH). Diazotizing IV.HCl at 0° and heating the diazonium solution at 50° give p-HOC6H4CH2CHMeCO2H (VI), needles, m. 102° (-)-VI, m. 99°, [α]D20 -18.5° (EtOH). m-HOC6H4CH2CHMeCO2H (VII) is an oil; (-)-VII, needles, m. 98°, [α]D20 -15.2° (EtOH). Diazotizing a 54% optically pure (-)-IV and heating the diazonium solution with CuH2 yield (-)-PhCH2CHMeCO2H, [α]D20 -14°, corresponding to an [α]D20 of -26° for the optically pure acid. Hydrogenating PhCH:CMeCO2H with NaHg and resolving the acid with quinine yield a quinine salt, m. 122°, [α]D20 116.2°; free (+)-acid, [α]D20 22.9°, d20 1.062; Me ester, b22 230°, d22 1.017, [α]D20 30.1°; (+)-amide, needles, m. 115°. The rotation dispersion of the substituted homohydratropic acids, their esters, and amides are listed in tables and show that the rotation direction is not changed by the entrance of m- and p-substituents. The experimental process involved the reaction of N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas: 456-12-2).Product Details of 456-12-2
N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas:456-12-2) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Product Details of 456-12-2
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics