558-42-9 , The common heterocyclic compound, 558-42-9, name is 1-Chloro-2-methyl-2-propanol, molecular formula is C4H9ClO, 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.
Sulfur powder (0.727 g, 22.71 mmol) was added to a solution of (2-Me2NCH2C6H4)Li (3.20 g, 22.71 mmol) in THF (50 mL) and the reaction mixture was stirred at room temperature for 6 h. Then 1-chloro-2-methyl-2-propanol (2.32 mL, rho = 1.06 g/mL, 22.71 mmol) was added at 0 ¡ãC and the reaction mixture was stirred for additional 18 h. The solvent was removed under vacuum and the remained product was treated with toluene. The solid residue was filtered off and the solvent was removed at reduced pressure. The resulting yellow oil was further distilled at a pressure of 2¡¤10-2 mbar and compound 1 was isolated as the fraction separated at 95 ¡ãC. Yield: 3.21 g (48.27percent). Anal. Found: C 65.34, H 8.91, N 5.81percent; Calc. for C13H21NOS (M = 239.38): C 65.23, H 8.84, N 5.85percent. 1H NMR (CDCl3): delta 1.21s (6H, CCH3), 2.23s (6H, NCH3), 3.08s (2H, CH2S), 3.56s (2H, CH2N), 6.53s, (br., 1H, OH), 7.10m (3H, H3-5), 7.56d (1H, H6, 3JHH 7.7 Hz). 13C NMR (CDCl3): delta 28.67s (NCH3), 44.73s (CCH3), 52.25s (CH2S), 63.06s (CH2N), 70.26s (COH), 126.92s (C4), 128.97s (C5), 131.15s (C3), 135.14s (C6), 138.93s (C2), 139.19s (C1); 1H NMR (acetone-d6): delta 1.23s (6H, NCH3), 2.22s (6H, CCH3), 3.09s (2H, CH2S), 3.56s (2H, CH2N), 5.11s (1H, OH), 7.16-7.31m (3H, H3-5), 7.56d (1H, H6, 3JHH = 7.6 Hz).
The synthetic route of 558-42-9 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Pop, Alexandra; Mitea, Raluca; Silvestru, Anca; Journal of Organometallic Chemistry; vol. 768; (2014); p. 121 – 127;,
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