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