Dolique, Roger published the artcileRelation between ultra-violet absorption and structure of derivatives of acetic and malonic acids, COA of Formula: C10H20O2, the publication is Annali di Chimica Applicata (1931), 425-521, database is CAplus.
The mutual influence on the absorption spectra of 2 neighboring chromophores diminishes with separation, and ceases when they are separated by more than 3 C atoms. In the preparation of disubstituted malonic esters the yield is improved if that substituent which contains a Ph nucleus is introduced first. Excess of Et malonate improves the yield in the preparation of monoalkyl derivatives of Et malonate. Improvements in the preparation of several of the following compounds are recorded. The Na derivative of Et n-butylmalonate (b12 127¡ã) with ¦Ã-phenylpropyl bromide gives Et ¦Ã-phenylpropylbutylmalonate, b15 212-3¡ã (35% yield), also obtained by reversing the order of introduction of the substituents (yield 33%), and purified by re-esterification of the acid, m. 137.5-8¡ã (yield of acid 91%). The heated acid gives ¦Á-(¦Ã-phenylpropyl)hexoic acid, m. 38¡ã, b19 215¡ã. Similar reactions give Et ethylbutylmalonate, b13 128¡ã, ¦Á-ethylhexoic acid, b755 222¡ã, b18 131¡ã (benzyl ester, b13 150¡ã; cf. Levene and Taylor, C. A. 17, 66), Et butylbenzylmalonate, b15 187¡ã (yield 35% from Et butylmalonate, or 52% from Et benzylmalonate) (Dox and Yoder, C. A. 16, 1934) (acid, m. 104.5¡ã), ¦Á-benzylhexoic acid, b14 185¡ã, b10 179¡ã (yield 95%) [Et ester, b756 274¡ã, b16 156¡ã (yield 82%); benzyl ester, b28 234-6¡ã, b16 222-3¡ã (yield 80%)], Et dibutylmalonate, b18 151-2¡ã (yield 55%; yield of acid 96%, ¦Á-butylhexoic acid, b15 149¡ã [Et ester, b752 218¡ã, b18 110¡ã (yield 84%), benzyl ester, b15 177¡ã, amide, m. 134.5¡ã (sublimes 100-10¡ã)] (cf. Levene and Cretcher, C. A. 12, 1546), Et ¦Â-phenylethylbutylmalonate, b15 203¡ã, b17 205¡ã (yield 34%, or 40%) [acid, m. 139¡ã (yield 86%)], ¦Á-(¦Â-phenylethyl)hexoic acid, b17 201-2¡ã, b28 238-9¡ã, Et dibenzylmalonate, b22 238¡ã (yield 75%) [acid, m. 174¡ã (yield 90%)], ¦Â-phenyl-¦Á-benzylpropionic acid, m. 91¡ã [Et ester, b18 202¡ã (yield 75%); benzyl ester, m. 81¡ã (yield 87%); amide, m. 129.5¡ã]. Et phenylmalonate gives Et phenylbutylmalonate (yield 58%), hydrolyzed to the acid, m. 153¡ã, and ¦Á-phenylhexoic acid, h20 182-3¡ã (also obtained by heating phenylbutylmalonic acid, and by hydrolysis of ¦Á-phenylhexonitrile, b20 151.1-2.5¡ã, obtained from CH2PhCN by means of NaNH2 and BuBr). Et ¦Á-ethylhexoate, reduced by Bouveault’s method (Bull. soc. chim. 9, 372(1893)), gives ¦Â-ethylhexanol, b758 180¡ã, b27 96-7¡ã, b18 89-90¡ã (yield 58%). Similarly are obtained ¦Â-butylhexanol (yield 63%; also obtained by similar reduction of ¦Á-butylhexoamide, yield 8%) (phenylurethan, m. 39¡ã), ¦Â-benzylhexanol, b27 170-1¡ã (yield 60%, also from the amide in small yield) (phenylurethan, m. 55.5¡ã). ¦Â-Phenyl-¦Á-benzylacetamide by similar treatment gives ¦Ã-phenyl-¦Â-benzylpropanol, m. 27-8¡ã, b10 197¡ã (phenylurethan, m. 94¡ã) (in better yield than from the ester), and a little ¦Ã-phenyl-¦Â-benzylpropylamine (Bz derivative, m. 104¡ã). ¦Á-Methyl-¦Á-ethylpentanol, b27 79-80¡ã, ¦Á-methyl-¦Á-benzylpentanol, b27 155¡ã, b18 144¡ã, ¦Â-Phenyl-¦Á-benzyl-¦Á-methylethanol (from AcOEt and CH2Ph.MgCl), b15 182¡ã, and ¦Á-benzyl-¦Á-methylpentanol (from Me.CO.CH2Ph and MgBuBr), b27 155¡ã, b18 144¡ã, could not be obtained optically pure.
Annali di Chimica Applicata published new progress about 3115-28-4. 3115-28-4 belongs to catalysis-chemistry, auxiliary class Aliphatic Chain, name is 2-Butylhexanoic acid, and the molecular formula is C10H20O2, COA of Formula: C10H20O2.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia