Benzyl Chloride → 3-Benzyloxypyridine

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Reaction Steps

9.5 g (10 mMol) 3-Hydroxy-pyridine and 9.45 ml (10 mMol) benzylchloride are dissolved in 50 ml CH2Cl2 at rt. 0.5 g Adogen 464® (Aldrich 63393-96-4) are added followed by dropwise addition of 50 ml of aq. NaOH solution (40% wt). The resulting yellow solution is stirred overnight, leading to formation of a white precipitate. The insolubles are filtered off and the filtrated is diluted with CH2Cl2 and H2O. The phases are separated and the aq. phase is repeatedly extracted with CH2Cl2. Combined organic extracts are dried, concentrated and the residual crude product is purified by flash chromatography (SiO2, CH2Cl2/MeOH 95:5) to give the title compound as a yellow oil: MS: [M+1]+=186; 1H MNR (CDCl3): δ ppm 8.42 (s, 1H), 8.26 (s, 1H), 7.55-7.38 (m, 5H), 7.30-7.19 (m, 2H), 5.17 (s, 2H).

Provenance & Evidence