Water → HCID 22153876, compound

Participants

Reaction Steps

12H-Dibenzo[d,g][1,3]dioxocin-6-carbonyl chloride (5.33 g, 19.5 mmol) is dissolved in toluene and added to a solution of 2-methoxyethanol (2.2 ml, 27.6 mmol) and 7 ml of triethylamine in toluene at 0°-10° C. under argon. The mixture is heated at reflux for 3 hours, cooled to room temperature, poured into 150 ml of water and extracted with 4×100 ml of ethyl acetate The resultant organic solution is washed with 5 percent hydrochloric acid, 5 percent sodium hydroxide and brine, dried with magnesium sulfate and filtered. The solvent is removed to give a brownish solid which is chromatographed on dry column silica gel, using ethyl ether/hexane (1:1) as the solvent, to give a yellowish oil. This oil is solidified, the solid is filtered and washed with ethyl ether/hexane to yield a white solid: mp 74°-76° C. IR (KBr) 1779, 1581 cm-1 ; 1H NMR (CDCl3) δ 3.42 (s, 3H, CH3), 3.3-4.0 (m, 3H, CH and OCH2), 4.35-4.8 (m, 3H, CH and OCH2), 5.1 (s, 1H, OCHO), 6.9-7.45 (m, 8H, aromatic).

Provenance & Evidence