Grinev, A. N. et al. published their research in Zhurnal Obshchei Khimii in 1959 | CAS: 28241-99-8

1-(5-Hydroxy-2-methylbenzofuran-3-yl)ethanone (cas: 28241-99-8) belongs to benzofurans derivatives.Benzofuran is one of the most significant oxygen-containing heterocycles consisting of fused benzene and furan ring, which are widely presented in various naturally occurring and synthetically active compounds. As benzofurans are prone to undergo ring opening of the heterocycle, examples of reduction of this type of aromatics by using dissolving metals are rather scarce.SDS of cas: 28241-99-8

Quinones. XXVI. Condensation of p-quinones with furoylacetic ester, acetylacetone and dibenzoylmethane was written by Grinev, A. N.;Bukhtenko, L. A.;Terent’ev, A. P.. And the article was included in Zhurnal Obshchei Khimii in 1959.SDS of cas: 28241-99-8 This article mentions the following:

To 20.5 g. ZnCl2 in 45 ml. EtOH was added 27.3 g. furoylacetic ester, followed by 10.8 g. p-benzoquinone (I). After 1 hr. at 100-10° there was isolated 0.6 g. benzodifuran, m. 254-5°, and 4 g. 2-furyl-3-carbethoxy-5-hydroxybenzofuran, m. 155-6° (this treated in dioxane with Me2SO4-NaOH gave the 5-methoxy analog, m. 65-5.5°). α-Naphthoquinone in the above condensation gave 2 furyl-3-carbethoxy-5-hydroxynaphthofuran, m. 215-16°; 5-Me ether m. 118-19°. Similarly Ac2CH2 and I gave a low yield of 2,6-dimethyl-3,7-diacetylbenzo[1,2-b;4,5-b’]difuran, m. 248-9°, and 60% 2-methyl-3-acetyl-5-hydroxybenzofuran, m. 234°. If I is gradually extracted into the reaction mixture of Ac2CH2, ZnCl2, absolute EtOH and absolute Et2O, the yield of the last product rises and that of the former product declines to zero. Reaction of Ac2CH2 with α-naphthoquinone in the presence of ZnCl2 as above gave 2-methyl-3-acetyl-5-hydroxynaphthofuran, m. 246-8°. Heating 8 g. 2,3-dichloro-p-benzoquinone with 4.5 g. imine of Ac2CH2 in CHCl3 45 min. gave 2-methyl-3-acetyl-6,7-dichloro-5-hydroxybenzofuran, 90%, m. 256-7°. Reaction of Bz2CH2 with α-naphthoquinone in the presence of ZnCl2 in EtOH gave 10:1 ratio of II, m. 174-5°, and 2-phenyl-3-benzoyl-5-hydroxynaphthofuran, m. 224-5°. The former treated with aqueous dioxane solution of NaOH gave a blue solution which with Me2SO4 gave III, m. 160-60.5°. In the experiment, the researchers used many compounds, for example, 1-(5-Hydroxy-2-methylbenzofuran-3-yl)ethanone (cas: 28241-99-8SDS of cas: 28241-99-8).

1-(5-Hydroxy-2-methylbenzofuran-3-yl)ethanone (cas: 28241-99-8) belongs to benzofurans derivatives.Benzofuran is one of the most significant oxygen-containing heterocycles consisting of fused benzene and furan ring, which are widely presented in various naturally occurring and synthetically active compounds. As benzofurans are prone to undergo ring opening of the heterocycle, examples of reduction of this type of aromatics by using dissolving metals are rather scarce.SDS of cas: 28241-99-8

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem