Ford, M. C. published the artcile3-Hydroxythiophene, Computed Properties of 17236-59-8, the publication is Journal of the Chemical Society (1956), 4985-7, database is CAplus.
The Grignard reagent from 3-bromothiophene (I) was treated with O with the production of a crude phenolic material, and two distillations gave the pure 3-hydroxythiophene (II), which was unstable, developing a reddish tinge and a disagreeable odor within a day, and finally resinifying. EtBr (18.5 g.) and 37 g. I (b759 157-8.5°) in 150 ml. Et2O added to a briskly reacting mixture of 18.5 g. EtBr, 13.7 g. Mg, and 200 ml. Et2O, the whole refluxed 18 hrs. under N and a solution of iso-PrMgBr (from 35 g. iso-PrBr) added, the mixture cooled to -10° and dry O passed in, the temperature maintained below 5°, after absorption had ceased the product set aside 20 hrs. at 5°, and then poured onto solid CO2, after addition of chilled 2N H2SO4, the Et2O layer separated, and the product purified gave 2.12 g. black product, which was stored over P2O5 and then distilled from glass wool giving II, yellow liquid, b0.01 38-9°, redistilled at 0.02 mm. to a colorless oil with a phenolic odor. With aqueous FeCl3 II gave an intense red color, and with diazotized PhNH2 in the presence of alkali, a dark red precipitate; benzoate (prepared by the Schotten-Baumann method), irregular prisms, m. 40° (from ligroine); 3,5-dinitrobenzoate, yellow prisms, m. 150° (from MeOH); phenylcarbamate, felted needles, m. 120° (from ligroine). These derivatives were stable. I (20 g.) was recovered from the Et2O solution of alkali-insoluble material. The infrared absorption curves were given for II in liquid film, 15% by volume CCl4, and 8% by volume CCl4. The absorption characteristic of an unsat. CO group definitely established the presence of the tautomeric 2,3-dihydro-3-oxothiophene (III). With increasing dilution the equilibrium was in favor of III; however, the strength of the OH band and the odor suggested that the pure substance must contain much II.
Journal of the 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, Computed Properties of 17236-59-8.
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