3-Acyl-4-hydroxycoumarins containing substituents in the benzene nucleus. IV. Syntheses of 3-acyl-5-methyl-4,7-dihydroxycoumarins and their antibacterial properties was written by Iguchi, Sadao;Utsugi, Nobuyuki. And the article was included in Yakugaku Zasshi in 1953.Product Details of 1634-34-0 This article mentions the following:
Orcinol (4 g.) and 3.7 g. CH2(CN)CO2Et in 30 ml. Et2O treated with 2 g. ZnCl2 and dry HCl gas passed in 2 hrs. gives 2.5 g. 7-hydroxy-5-methyl-2-oxo-4-imino-2,3-dihydro-4H-1-benzopyran (I), m. above 300° (decomposition); 2 g. I in 30 volumes dilute HCl (1:2) heated on a water bath, cooled, and the product filtered, washed with water, and recrystallized from hot water gives 1 g. 5-methyl-4,7-dihydroxycoumarin (II), needles, m. 266-7°. Reaction of 0.6 g. II and 0.26 g. AcCl in 8 ml. C5H5N and recrystallization of the product from alc. gives 0.4 g. 3-acetyl-5-methyl-4-hydroxy-7-acetoxycoumarin (III), needles, m. 149-50°, while the above reaction for 3 hrs. at 100-10° gives 0.1 g. III, and the mother liquor from III with 50% alc. yields 0.25 g. 3-acetyl-5-methyl-4,7-dihydroxycoumarin (IV), m. 242-3°. Heating III 30 min. on a water bath with 50 volumes 5% alc. KOH gives IV. Similarly, mild reaction of a 1:1 molar mixture of II and n-C9H19COCl and recrystallizing of the product from 7% alc. gives 7-decanoyl-5-methyl-4,7-dihydroxycoumarin (V), m. 153.5-4.5°; 3,7-didecanoyl-5-methyl-4,7-dihydroxycoumarin (VI), needles, m. 96-7°; 3-decanoyl-5-methyl-4,7-dihydroxycoumarin (VII), needles, m. 178-9°. Condensation of orcinol and AcCH2CO2Et (VIII) in the presence of concentrated H2SO4 gives 5-hydroxy-4,7-dimethylcoumarin, m. 252-3° similarly, resorcinol and VIII give 7-hydroxy-4-methylcoumarin, m. 184-5°. II (1 g.) in 10 ml. 10% KOH heated 1 hr. at 110-20°, cooled, acidified with HCl, and let stand give 0.35g.4,2,6-Me(HO)2C6H2Ac, leaves, m.157-8°. IV was effective in inhibiting the growth of Staphylococcus aureus at the dilution of 1:40000, being 10 times as potent as 3-acetyl-4,7-dihydroxy- and 3-acetyl-4-hydroxycoumarin used as the control. 3-Decanoyl derivatives could not be examined because of their difficult solubility None of these compounds showed any apparent effect on Escherichia coli. Ultraviolet absorption spectra of these compounds are given. In the experiment, the researchers used many compounds, for example, 2′,6′-Dihydroxy-4′-methylacetophenone (cas: 1634-34-0Product Details of 1634-34-0).
2′,6′-Dihydroxy-4′-methylacetophenone (cas: 1634-34-0) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Product Details of 1634-34-0
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts