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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《p-Mentha-1,5,8(9)-triene and its pyrolysis to dehydroocimene》. Authors are Alder, Kurt; Schumacher, Marianne.The article about the compound:(2-Methylthiazol-4-yl)methanolcas:76632-23-0,SMILESS:OCC1=CSC(C)=N1).Application of 76632-23-0. Through the article, more information about this compound (cas:76632-23-0) is conveyed.
LiAlH4 reduction of d(+)-carvone (I) gives 90% d-cis-carveol (II) which is dehydrated to p-mentha-1,5,8(9)-triene (III) whose structure is established, and which, on pyrolysis, gives 2,6-dimethyl-1,3,5,7-octatetraene (IV), called dehydroocimene. I (90 g.) in about 150 cc. ether added dropwise to 7.5 g. LiAlH4 in ether, warmed 1 hr., extracted with H2O then dilute H2SO4, and the ether layer evaporated and distilled gives carveol, b13 111-12°, which, distilled over KHSO4 in vacuo to 100° to remove volatile matter, leaves a residue which fractionated gives 60-5 g. III, b14 65-6.5°, nD20 1.4883, d20 0.8656, MR 44.69, λ 262 mμ (log ε 3.481). Ozonization of III in EtOAc gives CH2O in good yield. III with H and PtO2 takes up 6 H atoms/mole to give p-menthane, or warmed with 5% HCl in AcOH gives a quant. yield of p-cymene. III (6.5 g.) heated 15 hrs. in bomb with over 2 moles/mole III of di-Me acetylenedicarboxylate in 10 cc. PhMe at 140°, the product b0.04 90-120°, saponified and recrystallized from EtOAc gives the insoluble 3,6-dihydro-4-methyl-o-phthalic acid, m. 216°, and the soluble 4-methyl-o-phthalic acid, m. 159°, in equal amounts III adds to maleic anhydride in ether to give the adduct (V), m. 89-90°, whose hydrogenated derivative (VI), m. 91-2°, does not give CH2O on ozonization. V with 50% H2SO4 in dioxane 2-3 days gives a solution which extracted with ether gives the monolactone (VII), m. 184-5°; Me ester (VIII), m. 128-9°. Ozonization of VII in EtOAc gives acetone and an oxo acid, m. 215°; Me ester, m. 168°. VIII boiled with 10% NaOEt and the chief product lactonized with 50% H2SO4 in dioxane gives the dilactone (IX), m. 158°. The di-Me ester of V with 10% NaOEt gives a trans acid, m. 256°, whose dilactone, m. 164-5°, is not identical with IX. III (8 g.) refluxed 6-7 hrs. with 7 g. α-naphthoquinone in 15 cc. C6H6, the C6H6 removed, and the residue extracted with MeOH gives 80-90% adduct (X), m. 90-1°. Aeration of X in hot MeOH and alc. KOH gives an oil which boiled with EtOH gives 2-methylanthraquinone, m. 174-5°, and isoprene. Pyrolysis of III (105 g.) by distilling it at 12 mm. through a 75-cm. quartz tube at 520-40° at such a rate as to give one drop cracking product/sec. gives a hydrocarbon mixture which, redistilled in an N atm. at 36-72°/13 mm., gives mostly IV, nD20 1.4959, d20 0.8671, λ 303 mμ (log ε 3.934). IV is easily cyclized to p-cymene by distillation or by treatment with iodine in C6H6. IV (80 g.) in 100 cc. ether under N treated with 50 g. maleic anhydride 12 hrs. at room temperature, the unreacted IV removed by distillation, the residue taken up in Na2CO3 solution, extracted with ether, and acidified gives the ether-soluble adduct (XI), m. 191°. Ozonization of XI gives acetaldehyde while dehydrogenation of 2.5 g. XI with 0.8 g. S at 200° followed by extraction with Na2CO3 solution and acidification give 4,7-dimethylnaphthalene-1,2-dicarboxylic acid (XII), m. 213-14°; anhydride, m. 235-6°. Oxidation of 0.5 g. XII with 3 cc. HNO3 (d. 1.4) 16 hrs. at 140° in bomb followed by reaction with CH2N2 gives C6H(CO2Me)5, m. 147-8°. XI (1.2 g.) in CHCl3 with Br gives HBr and needles of C14H16O4Br2, m. 233°. Catalytic hydrogenation of XI in AcOH adds 1 mole H to give C14H20O4, m. 177-8°, which can be dehydrogenated by S to XII. Oxidation of XI by alk. KMnO4 gives a product of unknown constitution, C14H18O7, m. 282° (decomposition). IV (8 g.) refluxed 5-6 hrs. in C6H6 with 7 g. α-naphthoquinone, the C6H6 removed, and the residue recrystallized from MeOH gives a nearly quant. yield of adduct (XIII), needles, m. 115-16°. Dehydrogenation of XIII by air in 17% alc. KOH gives yellow needles of C20H16O2 (XIV), m. 145-6°. XIV is oxidized by HNO3 at 200° to give an acid which with CH2N2 gives tri-Me anthraquinone-1,2,3-tricarboxylate, m. 184-5°. Dehydrogenation of XIV by S at 190° gives 2′,3-dimethyl-1,2-benzanthraquinone (XV), m. 205°. XV is reduced by Zn and acetylated to C24H20O4, m. 175-6°, which is again oxidized by air in alc. KOH to XV. Addition of IV to di-Me acetylenedicarboxylate in C6H6, warming 3-4 hrs., and distilling give an ester, C16H18O4, m. 118-19°, whose saponification with alc. KOH gives an acid, m. 213-14°, which heated gives the anhydride, m. 197-8°, and which dehydrogenated with S and then boiled with acetic anhydrous gives 4,7-dimethylnaphthalene-1,2-dicarboxylic anhydride, m. 235-6°.
Compounds in my other articles are similar to this one((2-Methylthiazol-4-yl)methanol)Application of 76632-23-0, you can compare them to see their pros and cons in some ways,such as convenient, effective and so on.
Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem