Levene, P. A. published the artcileMaximum rotations of carboxylic acids containing a phenethyl group, COA of Formula: C11H14O2, the publication is Journal of Biological Chemistry (1935), 725-33, database is CAplus.
Ph(CH2)2CHMeEt (I) can be prepared from active AmOH without racemization and, on the basis of the maximum rotation of I, the maximum rotations of other members of the phenethyl series can be calculated Using this data as a basis, substances of the type Me(PhCH2CH2)CH(CH2)nCO2H, where n = 0 or an integer, were prepared Periodic fluctuations of the rotatory values as n increased were noted, thus parallelling the observations with the analogous Ph series and with carboxylic acids of the normal series. Ph(CH2)2CHMeCO2H, [M]D20 -51.20¡ã, was prepared by the CH2(CO2Et)2 (II) method and resolved by the cinchonidine salt from Me2CO. Ph(CH2)2CHMe(CH2)2OH and anhydrous HI followed by reduction with Raney’s catalyst in alk. MeOH gave I, b3 66-7¡ã, b13 96¡ã, d425 0.8563, nD25 1.4860, [M]D25 -17.72¡ã. I was also prepared from BzH and active AmMgBr via the intermediate PhCH(OH)CH2CHMeEt, b1 90¡ã, d425 0.9628, nD25 1.5097, [M]D25 -5.09¡ã, which with anhydrous HI overnight at -70¡ã and 48 hrs. at room temperature gave I, [M]D25 -35.1¡ã. The values for [M] of the following compounds are based on the parent AcOH, and values based on the parent hydrocarbon are found by using the factor 1.981 obtained from the above. Ph(CH2)2CHMe(CH2)2MgBr and CO2 gave Ph(CH2)2CHMe(CH2)2CO2H (III), b1 152-4¡ã. III was also prepared from Ph(CH2)2CHMeCH2CH2Br and II via the intermediate Ph(CH2)2CHMeCH2CH(CO2H)2, m. 96-8¡ã, which on heating at 180¡ã gave III, b1 162¡ã, d421.5 1.018, nD25 1.5066, [M]D21.5 -3.29¡ã, Et ester (IV), b2 122¡ã, d425 0.965, nD25 1.4872, [M]D25 -17.20¡ã. IV with Na and EtOH gave Ph(CH2)2CHMe(CH2)3OH, b10 155¡ã, d425 0.9477, nD25 1.5080, [M]D25 -10.13¡ã. Similarly Ph(CH2)2CHMe(CH2)3CO2H (V), b2.5 172¡ã, d425 1.0014, nD25 1.5039, [M]D25 -7.20¡ã, was prepared III reduced with PtO2 in AcOH gave C6H11(CH2)2CHMe(CH2)2CO2H, b10 180¡ã, d423 0.9528, nD25 1.4657, [M]D23 -2.51¡ã and V gave C6H11(CH2)2CHMe(CH2)3CO2H, b0.3 136-40¡ã, d425 0.9455, nD25 1.4685, [M]D25 -3.18¡ã. All values for [M] are maximum and for the homogeneous substance.
Journal of Biological Chemistry published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C11H14O2, COA of Formula: C11H14O2.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia