反应详情

A mixture of 4-hydroxy-3-methoxy-benzyl alcohol (17.4 g) and sodium cyanide (6.6 g) in dimethylformamide (250 ml) is stirred under an atmosphere of nitrogen for 3 hours at +120° C. The mixture is then cooled to +60° C. and toluene-4-sulfonic acid 3-phenyl-prop-2-ynyl ester (39 g) in dimethylformamid (50 ml)is added during 5 minutes. It is stirred at +65° C. for another 4 hours. Upon cooling water (800 ml) is added. The mixture is extracted with ethyl acetate (2×500 ml). The organic phases are washed with brine (2×500 ml), dried (MgSO4) and evaporated. The residue is purified by flash column chromatography on silica gel (ethyl acetate/hexane 1:3) and recrystallised from ethyl acetate/hexane. [3-Methoxy-4-(3-phenyl-prop-2-ynyloxy)-phenyl]-acetonitrile is obtained, m.p. 74-75° C.

1. temperatureThe mixture is then cooled to +60° C.
2. stirringIt is stirred at +65° C. for another 4 hours
3. additionis added
4. extractionThe mixture is extracted with ethyl acetate (2×500 ml)
5. washThe organic phases are washed with brine (2×500 ml)
6. dry with materialdried (MgSO4)
7. customevaporated
8. customThe residue is purified by flash column chromatography on silica gel (ethyl acetate/hexane 1:3)
9. customrecrystallised from ethyl acetate/hexane