100-86-7 , The common heterocyclic compound, 100-86-7, name is 2-Methyl-1-phenyl-2-propanol, molecular formula is C10H14O, 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.
To a cooled (0 C) solution (7.5 mL) of sulfuric acid H2SO4 (95 %), 2mL of trichloroacetonitrile in 28 mL of hexane was added dropwise and under magnetic stirring. Then, (1.5 g, 9.98 mmol) of tertiary alcohol 1 (commercial product) in 15 mL of hexane was added to the solution. After a return to room temperature, the resulting mixture was stirred under reflux for 2.5 h. Then, the solution was cooled at room temperature and versed on ice-cold water (50 mL) under magnetic stirring. The solution is alkalized with ammonia. The organic layer was extracted with dichloromethane (100mL), washed with a saturated aqueous NaCl solution, dried over sodium sulfate, and filtered. The solvent was removed in vacuo and the crude material was then purified by chromatography (silica gel, eluent dichloromethane/methanol 95:5) to afford the imine 6 as pure compound. Yield: 90%. Mp: 74 C. 1H NMR (CDCl3, 300 MHz): delta(ppm) 1.27 (s, 6H, 2-CH3), 2.74 (s, 2H, CH2), 7.22 (d, J=8.7 Hz, 1H), 7.30(m, 1H), 7.38 (m, 1H), 8.11 (d, J=7.8 Hz, 1H). 13C NMR (CDCl3, 75 MHz): delta 26.75 (2C), 39.02, 55.74, 97.67, 122.79, 126.16, 127.60, 128.70, 131.20, 138.31, 157.90. IR (KBr): upsilon 2970 cm -1 (CH3), 1690 cm -1 (C=N), 1618 cm -1 (Ar). HRMS-ES [M+Na]+ calc. for C12H12NCl3 Na 297.9933; found 297.9929.
The synthetic route of 100-86-7 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Aydi, Rihab; Kammoun, Majed; Synthetic Communications; vol. 46; 2; (2016); p. 134 – 144;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts