Autoxidation in the presence of alcohols and protons. III. Autoxidation of cyclenes, hydroarenes, and hydroheterocycles was written by Treibs, Wilhelm;Schoellner, Roll. And the article was included in Chemische Berichte in 1961.Computed Properties of C11H14O3 This article mentions the following:
Cyclohexene (I) and Tetralin (II) yield by autoxidation in the presence of alcs. and protons 伪-ketones and also under cleavage of the C-C bond neighboring the place of the O attack (CH2CH2-CHO)2 (III) and o-HOC6H4(CH2)3CHO (IV) which are stabilized as the acetals. The autoxidation of I yielded also as the result of a Prilesehayev-type reaction o-methoxycyclohexanol (V), 2-methoxy-1,3-cyclohexanediol (VI), and 3-methoxycyclohexene (VII). 1,2,3,4,10,11-Hexahydrodiphenylene oxide (VIII) yields similarly 1,2,3,4,11,12hexahydro-12-methoxydibenzodioxane (IX) and 1,2,3,4,10,11-hexahydro-10-methoxydiphenylene oxide (X). I (200 g.), 1500 cc. absolute MeOH, and 3 cc. concentrated H2SO4 irradiated 120 hrs. under O at 60掳 with ultraviolet light, neutralized with NaHCO3, decanted, and fractionated gave 7-8 g. VII, b. 135-6掳, n1D2 1.463, 14 g. distillate, b16 67-9掳 n1D0 1.4700, which chromatographed yielded cyclohexen-3-one, n2D0 1.4798 (2,4-dinitrophenylhydrazone, m. 164-6掳), and V, n1D0 1.4612, 3-4 g. cyclic di-Me acetal of III, b15 82-4掳, n2D0 1.432 [bis(2,4-dinitrophenylhydrazone) of III, m. 216-17掳], and 29 g. distillate, b15 98-118掳, which chromatographed gave 50-5% bis(dimethyl acetal) of III, b12 103-8掳 26-30% MeO2C(CH4)4CH(OMe)2 (2,4-dinitrophenylhydra zone m. 101掳), and 18-20% VI, n2D0 1.468. II (200 g.), 1500 cc. absolute MeOH, and 2.5 cc. concentrated H2SO4 irradiated 240 hrs. under O at 60掳, and the crude product (30 g.) distilled gave 11 g. 伪-tetralone, b12 130掳 (2,4-dinitrophenylhydrazone m. 257-8掳), 10 g. di-Me acetal of IV (2,4-dinitrophenylhydrazone of IV m. 148掳), and 15-20% o-HOC6H4(CH2)3CO2Me. Diphenylene oxide in absolute EtOH hydrogenated at 120掳/110 atm. gave 45-50% VIII, b0.04 51-2掳, n2D0 1.545, and some perhydrodiphenylene oxide, b20 130-4掳, and 0-phenylcyclohexanol, b20 149-53掳. VIII (150 g.) in 1500 cc. absolute MeOH and 2.5 cc. concn H2SO4 autoxidized under O during 96 hrs. at 60掳, neutralized with NH3, concentrated, and distilled gave a crude product, b0.3 93-6掳, n2D0 1.541, which chromatographed on Al2O3 yielded X, n2D0 1.5533, and IX. X (1 g.), 10 cc. 2N HCl, and 5 cc. MeOH refluxed 6 hrs., neutralized with NH3, concentrated, and chromatographed gave the 10-OH analog of X, m. 102掳. IX (1 g.), 20 cc. 0.1N HCl, and 5 cc. MeOH refluxed 6 hrs., and the crude product chromatographed on Al2O2 yielded 0.6 g. pure IX, m. 64-8掳, n8D0 1.542, and an unidentified material. Cumene (150 g.) autoxidized under the usual conditions during 360 hrs. gave 10-12 g. product containing 12-15% AcPh (2,4-dinitrophenylhydrazone m. 247掳). Com. cumene hydroperoxide (60%) (20 g.) added dropwise to 0.5 cc. concentrated H2SO4 in 250 cc. absolute MeOH, cooled, neutralized with NaHCO3, and fractionated yielded 6.7 g. cumene and 1.4 g. AcPh. In the experiment, the researchers used many compounds, for example, Methyl 4-(2-hydroxyphenyl)butanoate (cas: 93108-07-7Computed Properties of C11H14O3).
Methyl 4-(2-hydroxyphenyl)butanoate (cas: 93108-07-7) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Computed Properties of C11H14O3
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics