Pyridine → Toluene, alpha-chloro-2,3,4-trimethoxy-

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Reaction Steps

5 g (24.47 mmol) of 2,3,4-trimethoxybenzyl alcohol (Aldrich, Steinheim, FRG) are dissolved, under argon, in 13.9 ml of abs. methylene chloride, and this solution is treated with 0.278 ml of pyridine. 3.05 ml of thionyl chloride in 6.94 ml of abs. methylene chloride are added dropwise to this solution, while cooling slightly (ice/water), within the period of 20 min. During this procedure, the internal temperature rises to approximately 18°-23° C. The mixture is left to react subsequently for 45 min and the slightly yellow solution is then poured onto ice/water. After the phases have been separated, the organic phase is washed once each with 1N sulfuric acid and water. After drying over Na2SO4, and removing the solvent, the oily residue is distilled under HV (b.p.: 93°-95° C./0.07 Torr), and the title compound is obtained. 1H-NMR (220 MHz, CDCl3): 7.05 (d, 1H); 6.65 (d, 1H); 4.61 (s, 2H); 3.97 (s, 3H); 3.85 (s, 3H). HPLC: tRet =8.1 min (gradient II).

Provenance & Evidence