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Sodium metal (249mg, 10. [8MMOL)] was added to benzyl alcohol (30g, [278MMOL)] at room temperature under nitrogen and the reaction was stirred for 30 minutes. Methyl acrylate (25. 9ml, 259mmol) was then added dropwise and the reaction was stirred at room temperature for 18h. After quenching with saturated aqueous ammonium chloride solution [(200ML)] the mixture was extracted with ethyl acetate [(2X300M1)] and the combined organic extracts were washed with brine [(100MOI),] dried over magnesium sulphate and concentrated under reduced pressure. The residual oil was dissolved in ethanol [(300MOI)] and 1M aqueous sodium hydroxide solution [(300ML)] was added dropwise. After 3 hours the ethanol was removed under reduced pressure and the aqueous residue was washed with [DICHLOROMETHANE] [(200ML).] The aqueous phase was then acidified with 2N aqueous hydrochloric acid (150ml), extracted with [DICHLOROMETHANE] [(2X250ML)] 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 (300ML),] washed with diethylether [(300ML)] and the aqueous phase was acidified to pH1 using concentrated hydrochloric acid. The mixture was then extracted with [DICHLOROMETHANE] [(2X300M1)] and the combined organic extracts were dried over magnesium sulphate and concentrated under reduced pressure to provide the title compound (44.4g) as a colourless oil.
With sodium hydroxide; water; In ethanol; for 3h;
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 1 M 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. 1H NMR (300 MHz, CDCl3): delta=2.67 (t, 2H), 3.89 (t, 2H), 4.58 (s, 2H), 7.18 (m, 5H).
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