The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Preparation of o-dialkylbenzene》. Authors are Ogawa, Masaya; Tanaka, Giichi.The article about the compound:5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloridecas:148-51-6,SMILESS:OC1=C(C)C(CO)=CN=C1C.[H]Cl).Reference of 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride. Through the article, more information about this compound (cas:148-51-6) is conveyed.
1-Butyl-1-cyclohexene (45 g.) was oxidized 2 h. below 45° with 275 g. 80% HCO2H and with 50 g. 30% H2O2, the mixture neutralized and extracted with EtOAc, and the extract distilled to give 26 g. 1-butyl-l,2-cyclohexanediol (I), b2 115-18°. I (10 g.) in 50 cc. EtOH refluxed 30 min. with 0.5 cc. H2SO4, and the mixture distilled gave 4 g. 2-butylcyclohexanone (II), b7 76-8°. II was also prepared (51%) starting with 2-chlorocyclohexanone. II (0.5 mol) and 1 mol RMgX mixed at 0°, refluxed 5-7 h. at 30-5°, and distilled gave the following 1-alkyl-2-butylcyclohexanol (III) (alkyl, b.p./mm., d20, nD20, and % yield given): Bu, 115-17°/3.5, 0.8989, 1.4679, 43.2; octyl, 155-7°/4, 0.8850, 1.4683, 40; dodecyl, 184-5°/1, -, -, 37.4 (m. 46.5-7.5°). III heated 5 h. on oil bath with iodine and the product washed with 1% aqueous Na2S2O3 and distilled gave the following 1-alkyl-2-butyl-l-cyclohexenes (IV) (alkyl, b.p./mm., d20, nD20, and % yield given): Bu, 82-5°/3, 0.8410, 1.4635, 68.5; octyl, 148-51°/6, 0.8407, 1.4654, 85; dodecyl, 161-5°/1, 0.8407, 1.4654, 82.1. The IV were dehydrogenated over Pd-C at 220-80° to give the following 1-alkyl-2-butylbenzene (alkyl, b.p., d20, nD20, and % yield given): Bu, 256-7°, 0.8553, 1.4826, 57; octyl, 305-7°, 0.8570, 1.4827, 69; dodecyl, 358-9°, 0.8579, 1.4820, 46.
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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia