Diethyl Ether → HCID 11348064, compound

Temperature

0 °C

2,2′-Bis-(methoxymethoxy)bibenzene (7.5 g, 27.4 mmol) was dissolved in 300 mL of anhydrous Et2O in a 500 mL of three-necked bottle, while stirring, 80 mmol (50 mL, 1.6M solution in hexane) of nBuLi was added dropwise under Ar atmosphere, the mixture was stirred at room temperature for 2 h. After cooled to 0° C., DMF (20 mL, 260 mmol) in THF (20 mL) was added, and the solution was stirred at room temperature for another 4 h. Saturated NH4Cl (150 mL) was added to quench the reaction. The organic layer was separated and the aqueous phase was extracted with ethyl acetate (100 mL×3). The combined organic phase was washed with water (100 mL) and brine (100 mL) successively and dried over anhydrous MgSO4. Concentration with a rotary evaporator and subsequent chromatography on silica gel eluted with petroleum ether/ethyl acetate (3:1) afforded the product 3.925 g (47% yield) as a yellow oil. 1HNMR (300 MHz, CDCl3) δ (ppm) 3.15 (s, 6H), 4.81 (s, 4H), 7.37 (dd, J=0.9, 8.4 Hz, 2H), 7.67 (dd, J=1.8, 7.5 Hz, 2H), 7.93 (dd, J=1.8, 7.8 Hz, 2H), 10.44 (s, 2H). Physical data of the compound was consistent with that reported in literature.

1. stirringthe mixture was stirred at room temperature for 2 h
2. stirringthe solution was stirred at room temperature for another 4 h
3. customto quench
4. customthe reaction
5. customThe organic layer was separated
6. extractionthe aqueous phase was extracted with ethyl acetate (100 mL×3)
7. washThe combined organic phase was washed with water (100 mL) and brine (100 mL) successively
8. dry with materialdried over anhydrous MgSO4
9. concentrationConcentration
10. customwith a rotary evaporator and subsequent chromatography on silica gel
11. washeluted with petroleum ether/ethyl acetate (3:1)

ORD record

ord-e8b77090b82943dcba6b18397099ffe7

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07151070B2