Hurd, Charles D. published the artcileThienol, Quality Control of 17236-59-8, the publication is Journal of the American Chemical Society (1950), 5543-6, database is CAplus.
Thiophene-2-ol (I) was obtained by oxidizing 2-thienylmagnesium bromide (16.3 g. 2-bromothiophene, 18.5 g. iso-PrBr, and 6.5 g. Mg in 200 cc. ether) with dry O at 0°, hydrolyzing the product with dilute H2SO4, saturating with NaCl, and extracting the aqueous solution and the ether solution with 20% NaOH; 25% I, light yellow liquid, b6 80-84°, and 29% 2,2′-bithiophene, were obtained. I was vacuum-distilled in N; the colorless center fraction on cooling formed long needles, m. 7-9°, b760 217-19° (in N), d204 1.255, n20D 1.5644, mol. refraction 25.93, soluble in hexane 42%, in H2O 6%, miscible in all other common solvents. Also prepared were the acetate, solidified at -10° to -20°; benzoate, fine colorless crystals, m. 44-5°; Me 2-thienyl ether, 5-phenylazothienolophene-2-ol, m. 120-25°, and 2(or 4)-benzylidene-3(or 2)-butenothiolactone, m. 97.5-8.5°. The infrared and ultraviolet spectra gave evidence that I exists as keto-enol tautomers. It gives a red color with FeCl3, is a weak acid, undergoes characteristic reactions of the phenolic OH group, and reacts readily with diazotized amines in alk. solution The presence of the thiolactone was indicated by ring fission occurring in warm acid or alkali or during methylation with MeI or Me2SO4, and by the ready condensation with BzH. Under conditions sufficient for quant. monobromination of phenol, I consumed 1/3 equivalent of Br. Oxidation of 3-thienylmagnesium bromide gave a low yield of a steam-volatile liquid, very weakly acidic, having a phenolic odor and giving an intense vermilion with FeCl3; it apparently coupled with diazotized aniline. It is suggested that this compound was thiophene-3-ol.
Journal of the American Chemical Society published new progress about 17236-59-8. 17236-59-8 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Alcohol, name is Thiophen-3-ol, and the molecular formula is C4H4OS, Quality Control of 17236-59-8.
Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts