Canonica, Luigi published the artcileReformatskiǐ reactions. V. Further data on the stereochemical aspects of the Reformatskiǐ reaction, COA of Formula: C5H9IO2, the publication is Gazzetta Chimica Italiana (1955), 130-6, database is CAplus.
cf. C.A. 50, 6377d. In 3 cases already studied, α,β-disubstituted hydracrylic acids, obtained by alk. saponification of esters prepared by the Reformatskiǐ condensation, were found to be mixtures of 2 racemic stereoisomers, as predicted by theory. The present work shows that the esters are sterically unitary and that the inversion of configuration takes place within the esters themselves and precedes saponification The racemic HO acids are stable to alkalies. By the action of CH2N2 on the 2-iso-BuCH(OH)CH(CHMe2)CO2H, the corresponding esters are obtained. Their sapon, verifies the configuration of an ester formed by the Reformatskiǐ condensation. The experiments show also the influence of the temperature on the relative velocities of the reactions and the relative yields of the saponification products. Condensation of Me2CHCH2CHO (I) with Me2CHCHBrCO2Me (II) was carried out as with the Et ester (III) in earlier work, but with (Me2CH)2O as solvent. I (20 g.) and 40 g. II gave 33 g. crude product, which, rectified, yielded Me2CHCH2CH(OH)CH(CHMe2)CO2Me(IV), b3 103-4°, nD25 1.4421. III, IV, PhCH(OH)CH(CHMe2)CO2Et (V), and PhCH(OH)CHEtCO2Et (VI) were saponified by 10% NaOH at different temperatures (IV in MeOH; III, V, and VI in EtOH, and 10 cc. NaOH/g. ester). The time and temperature of saponification, yields of acids, % demolition to aldehydes, and % esters recovered are tabulated. Each acid (200 mg.) was refluxed 5 hrs. with 8 cc. 10% NaOH in MeOH, the free NaOH neutralized, the solution evaporated, H2SO4 added, and the mixture extracted with Et2O. After crystallization, almost 100% of the acid was recovered; no stereoisomeric acid was found. The form of Me2CHCH2CH(OH)CH(CHMe2)CO2H m. 88° (900 mg.) in 6 cc. Et2O treated slowly with 360 mg. CH2N2 in 7 cc. Et2O (kept ice-cold), evaporated in vacuo, and the ester and 10 cc. 10% NaOH in MeOH heated 5 hrs. at 65° and treated as usual give, from petr. ether, an acid fraction, m. 88°, and, from C6H6-petr. ether, a fraction, m. 126°. The mother liquor contains Me2CHCH2CO2H.
Gazzetta Chimica Italiana published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, COA of Formula: C5H9IO2.
Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com