Hydrochloric Acid → Ethyl [(prop-2-yn-1-yl)oxy]acetate

Participants

Reaction Steps

A solution of prop-2-yn-1-ol (815 g, 14.5 mol) in THF (1 L) is added dropwise to a suspension of NaH (60% content) (500 g) in THF (4 L) at 0° C. under nitrogen atmosphere. The stirring is continued at this temperature for 3 h before a solution of bromo-acetic acid ethylester (2.17 kg, 13.0 mol) in THF (2 L) is added dropwise over 1 h. After addition, the temperature is allowed to warm to RT and the reaction mixture is stirred for another 3 h. HCl (2 M, 8 L) is added into the reaction mixture, the organic layer is isolated and the aqueous layer is extracted with EtOAc (3×5 L). The combined organic layer is washed with brine (2 L), dried over anhydrous Na2SO4 and concentrated in vacuo. The crude oil is distilled to give the desired product. Yield: 1.6 kg. 1H NMR: (CDCl3) δ 4.31 (s, 2H), 4.23 (q, J=7.2 Hz, 2H), 4.19 (s, 2H), 2.47 (t, J=2.4 Hz, 1H), 1.29 (t, J=7.2 Hz, 3H).

Provenance & Evidence