Triphenylphosphine → 4-(2-(Benzyloxy)ethoxy)-2-methyl-1-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

3-Methyl-4-nitrophenol (17.48 g, 114 mmoles), 2-benzyloxyethanol (17.38 g, 114 mmoles, 16.22 ml) and triphenylphosphine (44.6 g, 170.2 mmoles) were dissolved in anhydrous tetrahydrofuran (200 ml) under nitrogen at room temperature. The stirred reaction mixture was then cooled to 0° C. and stirred for 10 minutes. Diisoproplyazo-dicarboxylate (23.49 g, 116.2 mmoles, 22.97 ml) was then added in one lot, and the reaction mixture was allowed to warm to room temperature and stirred overnight (16 hours). The solvent was removed under reduced pressure and the crude mixture was purified via column chromatography (silica gel, 5% ethyl acetate-hexane) to give the product. The remaining impurities were removed by means of crystallization from hexane ethyl acetate. The result crystals were filtered off and the mother liquor was evaporated under reduced pressure to give 21.56 g of 4-(2-(benzyloxy)ethoxy)-2-methyl-1-nitrobenzene. 1H-NMR (CDCl3) 8.08 (d, 1H), 7.38.7.31 (m, 3H), 6.82 (m, 2H), 4.65 (s, 2H), 4.23 (t, 2H), 3.87 (t, 2H), 2.63 (s, 3H).

Provenance & Evidence