Hydrochloric Acid → 2-[2-(2-Methoxyphenyl)ethoxy]ethanol

Participants

Reaction Steps

The solution of 10.1 g of [2-(2-methoxyphenyl)ethoxy]acetic acid in 50 ml of tetrahydrofuran is added dropwise at 0-5° C. to the stirred mixture of 1.76 g of lithium aluminium hydride in 50 ml of tetrahydrofuran. The reaction mixture is stirred at reflux over 5 hours and subsequently cooled to room temperature. 4 ml of water, 4 ml of 2N NaOH and once again 4 ml of water are successively added dropwise. The reaction mixture is poured onto 200 ml of 0.5 M HCl (cold) and extracted with ethyl acetate (2×200 ml). The organic phases are washed successively with water (200 ml) and brine (1×200 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.19 (1:1 EtOAc-heptane); Rt=3.32.

Provenance & Evidence