1,4-Dioxane → 1,3,5,7-Tetrahydrobenzo[1,2-c:4,5-c']difuran

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1,2,4,5-tetrakis-(bromomethyl)-benzene (150 g, 0.33 mmol) and 1,4-dioxane (2 L) was added a 55% aqueous solution of tetrabutylammonium hydroxide (640 mL) at room temperature, followed by stirring at 90° C. for 6 hours. The reaction mixture was allowed to cool to room temperature, and extracted with ethyl acetate after addition of a 2 N aqueous solution of hydrochloric acid (2 L). The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9) to give the title compound (35 g, 63% yield).

Provenance & Evidence