反应详情

A solution of potassium hydroxide (78.5 g, 0.5 mol) in water (100 mL) was added to a solution of hydroquinone (55.7 g, 0.5 mol) and 2-iodopropane (57.5 g, 0.33 mol) in ethanol. The dark brown solution was then refluxed for 16 hours Ethanol was removed and the aqueous phase was acidified with 2N HCl and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated to give over 70 g of crude material, which was triturated with dichloromethane and filtered. The filtrate was concentrated and purified on silica gel (ethyl acetate/hexane, 5˜35%) to give 23.0 g of product as a brown oil (46% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.30 (d, J=5.88 Hz, 6H) 4.30-4.50 (m, 1H) 4.78 (s, 1H) 6.66-6.86 (m, 4H), MS (ESI): m/z 151 (M−H),

1. customwas removed
2. extractionextracted with ethyl acetate (3×200 mL)
3. washThe combined organic layers were washed with brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated
7. customto give over 70 g of crude material, which
8. customwas triturated with dichloromethane
9. filtrationfiltered
10. concentrationThe filtrate was concentrated
11. custompurified on silica gel (ethyl acetate/hexane, 5˜35%)