Category: 6301-54-8

Electric Literature of 6301-54-8 , The common heterocyclic compound, 6301-54-8, name is 2-(Naphthalen-1-yl)propan-2-ol, molecular formula is C13H14O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

A mixture of 13 (31.66 g, 0.17 mol) and 2% sulfuric acid(600 mL) was stirred at reflux until the reaction completed as indicated by TLC analysis (typically within 2 h). On cooling to room temperature, the reaction mixture was extracted with CH2Cl2 (500 mL 3). The combined extracts were washed with 5% brine (500 mL), dried (Na2SO4) and evaporated on arotary evaporator to give a residue, which was purified by column chromatography to afford the pure product 2-(naphth-1-yl)propene (14) as a colorless oil (24.02 g, 84%). 1H NMR (CDCl3, 400 MHz) : 8.03-8.06 (m, 1H), 7.82-7.85(m, 1H), 7.74 (d, 1H, J = 8.0 Hz), 7.40-7.48 (m, 3H), 7.30(dd, 1H, J = 1.2 Hz and 3.4 Hz), 5.39-5.40 (m, 1H), 5.05 (d,1H, J = 1.2 Hz), 2.20 (s, 3H). The 1H NMR data were ingood agreement with those reported [18].

The synthetic route of 6301-54-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Xiansheng; Wu, Jingwei; Liu, Wei; Liu, Yuqiang; Xie, Yafei; Shang, Qian; Zhou, Zhixing; Xu, Weiren; Tang, Lida; Wang, Jianwu; Zhao, Guilong; Medicinal Chemistry; vol. 13; 3; (2017); p. 260 – 281;,
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Synthetic Route of 6301-54-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 6301-54-8 as follows.

General procedure: In a round bottom ask tted with three-way cock with septumwas placed benzyl alcohol analogue (1.0e1.5 mmol). The ask waslled with nitrogen after reducing pressure. After slight decom-pression to ease to the gas introduction, HI gas (0.5e2.0 equiv.) wasbrought in the vessel with syringe through the septum (the weightof HI gas was calculated the change of the weight of the equipmentbefore and after the introduction of HI gas). And nitrogen gas wasintroduced into vessel to release deference of pressure against at-mosphere. The mixture stood at 25C for 2 d. After reducingpressure to release HI gas, to the reaction mixture was addedsaturated Na2S2O3 (20 mL) and brine (15 mL). After being extractedwith CHCl3 or Et2O (15 mL 3), the organic layer was dried withMgSO4. After the concentration, ca. 10.0 mg of the residue wascombined with p-chlorobenzaldehyde (ca. 10.0 mg) as an internalstandard. And the mixture was measured with1H NMR to deter-mine the yield by the integration of methyl, methylene or methinepeak of the product and formyl peak of p-chlorobenzaldehyde(9.98 ppm). Furthermore, the reaction mixture included in p-chlorobenzaldehyde was subject to column chromatography onSiO2 to give the product.Iodinated products, (iodomethyl)benzene (2a),29(1-iodoethyl)benzene (2b),30and reduction products, diphenylmethane (3d),311,1-diphenylethane (3e),32triphenylmethane (3f),33wereassigned by the corresponding proton peaks at benzylic positionscompared with the chemical shift reported in the literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6301-54-8, its application will become more common.

Reference:
Article; Matsumoto, Shoji; Naito, Masafumi; Oseki, Takehisa; Akazome, Motohiro; Otani, Yasuhiko; Tetrahedron; vol. 73; 52; (2017); p. 7254 – 7259;,
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