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

Temperature

90 °C

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).

1. temperatureto cool to room temperature
2. extractionextracted with ethyl acetate
3. additionafter addition of a 2 N aqueous solution of hydrochloric acid (2 L)
4. washThe organic layer was washed with brine
5. dry with materialdried over anhydrous sodium sulfate
6. distillationthe solvent was distilled away under reduced pressure
7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9)

ORD record

ord-ad91ca44d7864a7bbbd3f56b983bcfa8

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592470B2