反应详情

To a stirred solution of Mg(OMe)2 (8% by weight in methanol 16.88 ml, 12.76 mM) was added 2-(1-hexenyl)phenol (3.44 g, 19.5 mmol) in toluene (18 ml). The reaction mixture was warmed to reflux and held at reflux for 2 hours. Toluene (18 ml) was added and the solvent distilled off until the reaction temperature rose to 93° C. A slurry of paraformaldehyde (1.8 g, 60 mmol) in toluene (18 ml) was added and the reaction heated at reflux for 3 hours. The reaction was allowed to cool to ambient temperature and stirred overnight. The reaction was diluted with toluene (20 ml) and washed with 2M aqueous H2SO4 (20 ml). The organic phase was washed with water until the aqueous phase was neutral in pH, dried (MgSO4) and evaporated. The residue was purified by chromatography (eluant: ethyl ether/hexane) to give 3-(1-hexenyl)-2-hydroxybenzaldehyde (2.32 g, 58%).

1. temperatureThe reaction mixture was warmed
2. temperatureto reflux
3. temperatureat reflux for 2 hours
4. distillationthe solvent distilled off until the reaction temperature
5. customrose to 93° C
6. temperaturethe reaction heated
7. temperatureat reflux for 3 hours
8. washwashed with 2M aqueous H2SO4 (20 ml)
9. washThe organic phase was washed with water until the aqueous phase
10. dry with materialdried (MgSO4)
11. customevaporated
12. customThe residue was purified by chromatography (eluant: ethyl ether/hexane)