4-Hydroxy-3-methylbenzonitrile (cas: 15777-70-5) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Application In Synthesis of 4-Hydroxy-3-methylbenzonitrile
Search for chemotherapeutic amidines. XIII. α,ω-Bis(p-amidinophenoxy)alkenes and -alkynes was written by Ashley, J. N.;MacDonald, R. D.. And the article was included in Journal of the Chemical Society in 1957.Application In Synthesis of 4-Hydroxy-3-methylbenzonitrile This article mentions the following:
Some α,ω-bis(p-amidinophenoxy)alkenes and -alkynes and their nuclear substituted derivatives were prepared for comparison with the saturated analogs. They had no value as trypanocides. Concentrated H2SO4 (2.9 cc.) added in one portion to 498 g. 4-bromo-2-methylphenol in 325 cc. Ac2O and the mixture refluxed 2 hrs. gave 562 g. 4-bromo-2-methylphenyl acetate (I), colorless oil, b12 132°. CuCN (145 g.) was added during 0.5 hr. to 100 cc. dry C5H5N at 90° (the internal temperature rose to 140°), the mixture stirred 10 min. longer and 275 g. I added, the bath temperature raised rapidly to 200° (an endothermic reaction occurred), and the mixture heated 3 hrs. at 228-30° and distilled at 60-170°/20-30 mm. This distillate poured on ice and concentrated HCl gave 177 g. 4-cyano-2-methylphenyl acetate (II), m. 75-6°. Hydrolysis of II gave 87% 4-cyano-2-methylphenol, m. 93-5°, b12 180-2°. 1,4-Dichloro-2-butyne (III) (70%), b10 52-2.5°, 1,4-dibromobut-2-yne (IV) (85%), and 1,6-dibromohexa-2,4-diyne (V) (79%), m. 18-19°, were prepared by recorded methods. cis-1,4-Dihydroxy-2-butene (b15 128-30°) gave 54% cis-dibromide (VI), b0.8 33.5-4.0°. VI heated with a trace of iodine 1 hr. at 130-40° gave the trans isomer, plates, m. 52-3.5° (from ligroine). [2,4-R(NC)C6H3]2X (VII) were prepared by the following methods: (A) an alc. solution of the cyanophenol (2.2 moles) followed by 1 mole IV added to 2.2 moles Na in dry alc. (20 cc. per g. of Na), the mixture refluxed overnight, cooled, and filtered, the residue washed with H2O, and recrystallized gave VII; (B) 22 g. V was added to a stirred suspension of 17.2 g. NaHCO3 in 24.3 g. p-cyanophenol in 100 cc. Me2CO, the mixture refluxed overnight, cooled, filtered, and the residue washed with H2O, and crystallized from AcOH; (C) 1 mole III refluxed overnight with 2.2 moles of the cyanophenol in 2.2 mole KOH and alc. gave VII (substituents X and R, method, % yield, m.p. given): (OCH2C)2, H, A, 60, 159-61°; (OCH2C)2, Me, A, 40, 166-7°; (OCH2C)2, Cl, C, 54, 224-6°; (OCH2C)2, Br, C, 50, 220-2°; (OCH2C)2, H, B, 49, 195-7°; trans-OCH2CH:CHCH2O, H, A, 70, 204-6°; trans-OCH2CH:CHCH2O, Cl, C, 61, 207-9°. VII suspended or dissolved in the appropriate alc., and the mixture saturated with HCl at 0-10°, the diimidoate di-HCl salts gradually formed, and after several days collected, dried, and heated 5-6 hrs. at 50-60° with saturated alt. NH3 gave the following α,ω-bis(p-amidinophenoxy)alkenes and alkynes {4,2-R[H2NC(:NH)]C6H3}2X (substituents X and R, salt, alc. (and diluent) used in preparation of diimidoate, solvent for crystallization, m.p. given): (OCH2C)2, H, 2HCl.2H2O, alc. (CHCl3), MeOH-OCMe2, 245-7°; (OCH2C)2, Me, 2Me2SO3H, alc. (CHCl3), MeOH, 308-10°; (OCH2C)2, 2HO(CH2)2SO3H.0.5H2O, Cl, alc. (dioxane), MeOH-Et2O, 243-5°; (OCH2C)2, Br, 2HO(CH2)2SO3H, alc., MeOH, 253-5°; (OCH2C)2, H, 2HO(CH2)2SO3H, alc., dilute HO(CH2)2SO3H, 272-4°; trans-OCH2CH:CHCH2O, H, 2MeSO3H, alc. dilute, MeSO3H, 274-6°; trans-OCH2CH:CHCH2O, Cl, 2HO(CH2)2SO3H, HO(CH2)2OEt, MeOH, 236-8°. 1,4-Bis(p-amidinophenoxy)-2-butyne di-HCl salt in MeOH was hydrogenated over 10% Pd-CaCO3 at room temperature until 1 mole H was taken up and the diamidine di-HCl salt converted to the dimethanesulfonate in 70% yield, m. 232-4° (from MeOH). cis-1,4-Bis(4-amidino-2-chlorophenoxy)-2-butene was prepared similarly, and the gummy di-HCl salt which was precipitated by addition of Me2CO as a powder after trituration with Me2CO converted to the 2HO(CH2)2SO3H salt, m. 218-20°. In the experiment, the researchers used many compounds, for example, 4-Hydroxy-3-methylbenzonitrile (cas: 15777-70-5Application In Synthesis of 4-Hydroxy-3-methylbenzonitrile).
4-Hydroxy-3-methylbenzonitrile (cas: 15777-70-5) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Application In Synthesis of 4-Hydroxy-3-methylbenzonitrile
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts