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.
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.
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Alcohols – Chemistry LibreTexts