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.Category: alcohols-buliding-blocks Organoboron compounds are less toxic than organostannane reagents, and unlike alkynylzinc and magnesium, many organoboron compounds possess remarkable oxidative and thermal stabilities.
The author of 《Some derivatives of catechol and pyrogallol. I》 were Haworth, Robert D.; Woodcock, David. And the article was published in Journal of the Chemical Society in 1946. Category: alcohols-buliding-blocks The author mentioned the following in the article:
In view of the vesicancy attributed to pyrocatechol (I) derivatives occurring in natural lacquers, a number of 3- and 4-acyl- and -alkyl-pyrocatechols and -pyrogallols containing C4 to C18 side chains have been synthesized and tested. 1,2,3-C6H3(OH)3 (1 mol.), 2.1 mols. aliphatic acid, and 1 mol. anhydrous ZnCl2 are heated 2 h. at 135-40°, the cooled mixture treated with dilute HCl, the product taken up in ether and, after washing with H2O, distilled at 0.5 mm.; the following 4-acylpyrogallols were thus prepared: butyryl, m. 90-1°, 60% (Hart and Woodruff, C.A. 30, 8186.8, give 101°); hexanoyl, m. 72-4°, 50% (H. and W., loc. cit., give 86°); octanoyl, m. 73-4°, 40%; hendecanoyl, m. 76-7°, 35%; dodecanoyl, m. 76-7°, 30%; tetradecanoyl, m. 82-4°, 25%; hexadecanoyl, m. 89-90°, 30%; octadecanoyl, m. 91-3°, 25%. Clemmensen reduction (1 part phenol, 5 parts amalgamated Zn, and 5 parts concentrated HCl refluxed 24 h.) gives 50-65% 4-alkylpyrogallols: octyl, m. 106-7°; nonyl, m. 109-10°; hendecyl, m. 110-11°; dodecyl, m. 109-10°; tetradecyl, m. 112-13°; hexadecyl, m. 116°; octadecyl, m. 114-15°. 4-Acylcatechols were prepared by heating equal weights of I, the acid, and anhydrous ZnCl2 at 135-40° for 2 h.: hendecanoyl, m. 105°, 15%; dodecanoyl, m. 97-8°, 20%; tetradecanoyl, m. 98-9°, 20%; hexadecanoyl, m. 99-100°, 10%; octadecanoyl, m. 100-1°, 10% (Rosenmund and Lohfert, C.A. 23, 2161, give 70°). In the preparation of 4-nonanoylcatechol (m. 92-3°, 40%), 1 mol. I diester, 1 mol. I, and 2 mols. AlCl3 in 20 mols. PhNO2 were heated 2 h. at 80-100°; for the preparation of 4-heptanoylcatechol (m. 93-4°, 50%; Miller, et al., C.A. 32, 1669.2, give 79°), 1 mol. I and 1.5 mols. AlCl3 in 20 parts CS2 were gradually treated with 1 mol. acid chloride, heated to 40-50°, the solvent removed, and the residue heated at 150° for 4 h. Because of the inaccessibility of the higher aliphatic acids with an odd number of C atoms, (MeO)2C6H3CHO was reacted with RMgX and the product dehydrated with KHSO4 at 180°; the following were obtained crystalline: 17-(3,4-dimethoxyphenyl)-1-heptadecene, m. 40-1°, 60%; 15-(2,3-dimethoxyphenyl)-1-pentadecene, b0.5 190°, m. 52°, 35%. Catalytic reduction (10% Pd-C in EtOH for 4-12 h.) yields 100% of 1-(3,4-dimethoxyphenyl)heptadecane, m. 53-4°, and 1-(2,3-dimethoxyphenyl)pentadecane, m. 34-6°. These compounds were demethylated with HI or HBr (3 conditions given). The following 4-alkylpyrocatechols were prepared by Clemmensen reduction: Bu, m. 39-41°; Am, m. 57-9°; heptyl, m. 65-7° (M., loc. cit., gives 40°); octyl, m. 57-8° (M. gives 40°); nonyl, m. 68°; hendecyl, m. 81-2°; dodecyl; m. 75-6°; tetradecyl, m. 65-7°; hexadecyl, m. 75-6°; octadecyl, m. 78-9°. The 3-alkylpyrocatechols were prepared by demethylation: Bu, m. 33-6°; Am, m. 34-5°; hexyl, m. 30-1°, heptyl, solid at 5°; octyl, b0.4 135-40°. None of the compounds produced vesication but several caused erythema. Pyrocatechols are more irritant than the corresponding pyrogallol derivatives In the 4-alkylpyrocatechol series, the members from Bu to octyl have approx. the same activity, which decreases with increasing length of side chain; in the 3-alkyl series, the optimum activity is found in the 3-heptyl derivative, but there is no pronounced difference in the activity of the 3- and 4-alkyl series. Acylpyrocatechols and -pyrogallols are completely inactive. The slight activity of 4-amylresorcinol suggests that the irritant properties are not limited to the I series. In the experiment, the researchers used 4-Butylbenzene-1,2-diol(cas: 2525-05-5Category: alcohols-buliding-blocks)
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.Category: alcohols-buliding-blocks 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