In 1954,Nippon Nogei Kagaku Kaishi included an article by Okuma, Kazuhiko; Tamura, Saburo. COA of Formula: C10H14O2. The article was titled 《Inhibition of the autoxidation of fats and oils. XI. Syntheses of some ω-(2,5-dihydroxyphenyl)alkanoic esters and ω,ω’-bis(2,5-dihydroxyphenyl)alkanes》. The information in the text is summarized as follows:
Since hydroquinone derivatives seemed to have generally higher antioxidant activity than catechol derivatives, the 2,5-dihydroxyphenyl derivatives rather than 3,4-dihydroxyphenyl derivatives were synthesized as possible antioxidants. Me-γ-(2,5-dihydroxyphenyl)butyrate (X) was obtained by esterifying the corresponding free acid (XI). Fieser, et al. (C.A. 35, 889), could not prepare XI by demethylation of γ-(2,5-dimethoxyphenyl)butyric acid. This was presumed to be due to cyclization. β-(2,5-Dimethoxybenzoyl)propionic acid (XII), m. 101-2°, prepared according to F., et al. (loc. cit.), was demethylated with HI to β-(2,5-dihydroxybenzoyl)propionic acid (XIII), m. 180-2°, yellow columns in 81% yield. XIII was hydrogenated with Zn-Hg to XI, m. 131-2°, in low yield (1 g. from 20 g. XIII). XI (0.3 g.) refluxed with MeOH and H2SO4 gave 71.8% X, m. 66-7°, tabular crystals. XII (10 g.) demethylated with 13 g. AlCl3 and 100 cc. PhCl did not give XIII, but β-(2-hydroxy-5-methoxybenzoyl)propionic acid, m. 140° [the positions of OH and OMe in the benzene nucleus were not determined, but were assumed by analogy to the formation of 2-hydroxy-5-methoxy-β-chlorochalcone (Simonis and Danishevski, C.A. 21, 1255]). Hydroquinone di-Me ether (69 g.) with polymeric adipic anhydride, m. 75° (prepared from 73 g. adipic acid and 300 cc. Ac2O), in the presence of 140 g. AlCl3 gave 55 g. δ-(2,5-dimethoxybenzoyl)valeric acid, m. 78-80°, needles, 30 g. of which hydrogenated with 72 g. Zn amalgam gave 14.7 g. ε-(2,5-dimethoxyphenyl)hexanoic acid, b5 200-2°, m. 64-7°. This was demethylated with HI to give ε-(2,5-dihydroxyphenyl)hexanoic acid, m. 112-13° [m. 96.8-97.6°, by Fieser, et al. (loc. cit.), but the analysis conformed with the theoretical]. This was methylated to give Me ester, which could not be crystallized (analysis differed somewhat from the theoretical). Hydroquinone di-Me ether (30 g.) with 14.6 g. adipic acid and 25 cc. SOCl2 gave 12 g. 1,4-bis(2,5-dimethoxybenzoyl)butane, m. 105-6°, needles, 5 g. of which with 2.5 cc. 80% hydrazine hydrate gave 3.7 g. yellow 1,6-bis(2,5-dimethoxyphenyl)hexane. This was not purified, but was demethylated with HI to give 1,6-bis(2,5-dihydroxyphenyl)hexane, m. 159-60°, scales. Similarly, 1,10-bis(2,5-dihydroxyphenyl)decane, m. 148-50°, scales, was obtained in 46.3% yield by demethylation with HI of 1,10-bis(2,5-dimethoxyphenyl)decane, m. 76-8°, needles, in 56.2% yield from 1,8-bis(2,5-dimethoxybenzoyl)octane, m. 99-100°, needles, prepared from hydroquinone di-Me ether and sebacoyl chloride. The experimental process involved the reaction of 4-Butylbenzene-1,2-diol(cas: 2525-05-5COA of Formula: C10H14O2)
4-Butylbenzene-1,2-diol(cas: 2525-05-5) belongs to organoboron compounds. Organoboron compounds are versatile intermediates and as such are some of the most important classes of reagents in modern organic chemistry.COA of Formula: C10H14O2 Organoboron compounds are less toxic than organostannane reagents, and unlike alkynylzinc and magnesium, many organoboron compounds possess remarkable oxidative and thermal stabilities.
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts