Catechol → 2-(3-Methoxypropyloxy)-phenol

Participants

Reaction Steps

A solution of 22 g of pyrocatechol in 80 ml of N,N-dimethylformamide is added at room temperature in the course of 30 minutes to a suspension of 8.4 g of sodium hydride (60% dispersion in mineral oil) in 300 ml of dimethylformamide, and the reaction mixture is stirred for 1 hour at room temperature. A solution of 49.3 g of 3-bromopropyl methyl ether in 80 ml of dimethylformamide is then added dropwise thereto. The reaction mixture is stirred further for 80 hours at room temperature and then concentrated by evaporation under reduced pressure at a bath temperature of 30° C. The residue is partitioned between diethyl ether and water. The organic phases are combined, dried over magnesium sulfate and concentrated by evaporation and the residue is purified by means of FC (100 g of silica gel, hexane/dichloromethane 5:95) to yield the title compound: Rf (dichloromethane/diethyl ether 96:4)=0.35; HPLC Rt =11.2 minutes.

Provenance & Evidence