反应详情

A mixture of 4-nitrophenol (14.0 g., 0.10 mol), 3-chloropropionic acid (10.8 g., 0.10 mol) and potassium hydroxide (11.2 g., 0.20 mol) in water and ethanol is heated at reflux temperature for 2 hours, cooled to ambient temperature, acidified with concentrated HCl to pH˜1, and extracted with ethyl acetate. The organic phase is washed with a saturated aqueous solution of sodium bicarbonate. The aqueous bicarbonate phase is acidified with concentrated hydrochloric acid, and extracted with ethyl acetate. The final ethyl acetate extract is washed with brine, dried over MgSO4 and concentrated in vacuo. The resultant residue is crystallized from ethyl ether and hexane to afford the title compound as an off-white crystalline solid, 5.3 g (25% yield), mp 117-118° C., identified by NMR and mass spectral analyses.

1. temperatureis heated
2. temperatureat reflux temperature for 2 hours
3. extractionextracted with ethyl acetate
4. washThe organic phase is washed with a saturated aqueous solution of sodium bicarbonate
5. extractionextracted with ethyl acetate
6. extractionThe final ethyl acetate extract
7. washis washed with brine
8. dry with materialdried over MgSO4
9. concentrationconcentrated in vacuo
10. customThe resultant residue is crystallized from ethyl ether and hexane