Braun, J. V. published the artcileSyntheses in the aliphatic-aromatic series. XII, COA of Formula: C11H14O2, the publication is Berichte der Deutschen Chemischen Gesellschaft (1914), 262-9, database is CAplus.
cf. C. A., 7, 2567. The following compounds were prepared to determine whether the introduction of a Me group in the CH2 adjacent to CH2OH or CHO in the side chain of aliphatic-aromatic alcs. and aldehydes has in general a greater influence on the odor than when it is introduced nearer to the aromatic radical, as was found in the case of PhCH2CH2CH3OH and PhCH2CH3CHO: It was found that the methylation does change the odor but at the same time it weakens it so extraordinarily that shades cannot be distinguished. Diethyl phenethylmethylmalonate, in 77% yield from Ph(CH2)2CH(CO2Et)2 and MeI, b20 192¡ã, hydrolyzed by aqueous alc. KOH to the acid, m. 160¡ã, which at 165¡ã, gives ¦Á-methyl-¦Ã-phenylbutyric acid, b19 180¡ã (different from Willgerodt and Merck’s compound (C. A., 4,903)); its ethyl ester, b17 143-4¡ã, with Na and alc. gives 60% of ¦Â-methyl-¦Ã-phenylbutyl alcohol, viscous oil, b18 145-8¡ã, d420 0.9719, has a faint odor somewhat more pleasant than that of Ph(CH2)4OH.Di-ethyl ¦Ä-phenylpropylmethylmalonate, in 80% yield from Ph(CH2)2CH(CO2Et)2, b18, 194¡ã; with 2 mols. of hot aqueous alc.KOH, even after 2.5. hrs., it gives chiefly the monoethyl ester, oil which loses CO2 on distillation, with formation of ethyl ¦Á-methyl-¦Ä-phenyl. valerate, b17 158¡ã, hydrolyzed by alks. to the acid, b19, 190¡ã, and reduced by Na and alc. to ¦Â-methyl-l¦Ä-phenylamyl alcohol, b20 159-60¡ã, d420 0.9642, has an odor much fainter but similar to that of Ph(CH2)4OH. Its chloride, obtained by heating the alc. with 2 parts fuming HCl at 120¡ã b12 140-2¡ã, has not as pleasant an odor as that of Ph(CH2)21Cl, gives quant. with NaI the iodide, b20 160-6¡ã, which with AgNO2 gives approx. equal amounts of nitrite, b16, about 130¡ã, and of nitro compound, yellow, b. 172-8¡ã; when the latter is reduced with SnCl2 and the resulting oxime is b. 0.5 hr. with 15 % H2SO4 there is obtained ¦Á-methyl-¦Ä-phenylvaleraldehyde, b21 148-52¡ã (50% yield); its odor is much fainter and not so characteristically lemon-like as that of Ph(CH2)4CHO. Diethyl ¦Ã-phenylisobutylmalonate, in 80% yield from CH2(CO2Et)2 and PhCH2CHMeCH2Br, b11 189¡ã, gives 80% of diethyl phenylisobutylmethylmalonate, b12 192-4¡ã. Free acid, oil, gives phenylisobutylmethylacetic acid, b. 282-4¡ã; ethyl ester, b25 154¡ã. ¦Â,¦Ã-Dimethyl- ¦Ò-phenylamyl alcohol (55-60% yield), b17 156-8¡ã, d420 0.9549, has a fainter odor even than the ¦Â-monomethyl compound Chloride, b20 146-8¡ã, has an even less pleasant odor than the mono-Me compound Iodide, b20 163-6¡ã. Nitro compound, b20 176-81¡ã. ¦Á,¦Ã-Di- methyl-¦Ä-valeraldehyde, b20 151-6¡ã.
Berichte der Deutschen Chemischen Gesellschaft 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