2-Hydroxy-4-methoxybenzophenone → HCID 69082653, compound

Participants

Reaction Conditions

Reaction Steps

A 500 mL three-neck flask was charged with (2-hydroxy-4-methoxyphenyl)(phenyl) methanone (100.0 g; 0.4381 mol), 1-bromo-3-chloropropane (82.78 g; 0.5258 mol) and 4-methyl-2-pentanone (250 mL). Anhydrous potassium carbonate (66.61 g; 0.4819 mol) was added and the reaction mixture was stirred at reflux (120° C.) for 10 h. The reaction mixture was filtered hot and the inorganic solids were washed with 4-methyl-2-pentanone (2×100 mL). The filtrate was charged into a mixture of neat diethanolamine (161.2 g; 1.533 mol) and sodium iodide (6.57 g; 43.81 mmol). The reaction mixture heated to reflux (122° C.) for 24 h. The reaction mixture was cooled to room temperature and diluted with water (500 mL). The resulting emulsion was extracted with 4-methyl-2-pentanone (2×200 mL). The aqueous phase was discarded and the organic phase was extracted with 1 M HCl (2×500 mL). The aqueous phase was taken to pH 12 with 50% aqueous NaOH. The resulting emulsion was extracted with 4-methyl-2-pentanone (3×200 mL). The organic phase was separated, dried (MgSO4), filtered and the solvent removed in vacuo. This provides (2-{3-[bis(2-hydroxyethyl)amino]propoxy}-4-methoxyphenyl)(phenyl)methanone (light yellow oil; 90.4 g; 55% yield over 3 steps).

Provenance & Evidence