Orcinol → 3-Methyl-5-(quinolin-2-ylmethoxy)-phenol

Participants

Reaction Steps

2-(Chloromethyl)-quinoline hydrochloride (1.28 g, 6.0 mmol), orcinol (568 mg, 4.0 mmol), K2CO3 (1.68 g, 12.0 mmol) and a catalytic amount of tetrabutylammonium iodide (˜10 mg) are dissolved/suspended in anhyd. DMF (10 mL) and heated at 50° C. overnight. The reaction is cooled to r.t. and partitioned between water (100 mL) and ethyl ether (100 mL). The pH of the aqueous layer is adjusted to ˜5 and further extracted with ethyl ether (100 mL). The organic fractions are pooled and washed with brine (2×100 mL), dried over MgSO4, filtered and preadsorbed onto silica gel. The crude preadsorbed material is purified by flash chromatography (silica, 20% ethyl acetate in hexanes) to give the title compound. This product (approx. 80% purity, remainder is 2-methylquinoline) is used without further purification. MS (ESI) 266 (M+H)+.

Provenance & Evidence