反应详情

Sodium metal (249 mg, 10.8 mmol) was added to benzyl alcohol (30 g, 278 mmol) at room temperature under nitrogen and the reaction was stirred for 30 minutes. Methyl acrylate (25.9 ml, 259 mmol) was then added dropwise and the reaction was stirred at room temperature for 18 h. After quenching with saturated aqueous ammonium chloride solution (200 ml) the mixture was extracted with ethyl acetate (2×300 ml) and the combined organic extracts were washed with brine (100 ml), dried over magnesium sulphate and concentrated under reduced pressure. The residual oil was dissolved in ethanol (300 ml) and 1M aqueous sodium hydroxide solution (300 ml) was added dropwise. After 3 hours the ethanol was removed under reduced pressure and the aqueous residue was washed with dichloromethane (200 ml). The aqueous phase was then acidified with 2N aqueous hydrochloric acid (150 ml), extracted with dichloromethane (2×250 ml) and the combined organic extracts were dried over magnesium sulphate and concentrated under reduced pressure. The residual oil was dissolved in 10% aqueous potassium carbonate solution (300 ml), washed with diethylether (300 ml) and the aqueous phase was acidified to pH1 using concentrated hydrochloric acid. The mixture was then extracted with dichloromethane (2×300 ml) and the combined organic extracts were dried over magnesium sulphate and concentrated under reduced pressure to provide the title compound (44.4 g) as a colourless oil.

1. stirringthe reaction was stirred at room temperature for 18 h
2. customAfter quenching with saturated aqueous ammonium chloride solution (200 ml) the mixture
3. extractionwas extracted with ethyl acetate (2×300 ml)
4. washthe combined organic extracts were washed with brine (100 ml)
5. dry with materialdried over magnesium sulphate
6. concentrationconcentrated under reduced pressure
7. dissolutionThe residual oil was dissolved in ethanol (300 ml)
8. addition1M aqueous sodium hydroxide solution (300 ml) was added dropwise
9. customAfter 3 hours the ethanol was removed under reduced pressure
10. washthe aqueous residue was washed with dichloromethane (200 ml)
11. extractionextracted with dichloromethane (2×250 ml)
12. dry with materialthe combined organic extracts were dried over magnesium sulphate
13. concentrationconcentrated under reduced pressure
14. dissolutionThe residual oil was dissolved in 10% aqueous potassium carbonate solution (300 ml)
15. washwashed with diethylether (300 ml)
16. extractionThe mixture was then extracted with dichloromethane (2×300 ml)
17. dry with materialthe combined organic extracts were dried over magnesium sulphate
18. concentrationconcentrated under reduced pressure