反应详情

Methyl 2-(4-chlorophenyl)acetate (36.7 g, 199 mmol) and paraformaldehyde (6.27 g, 209 mmol) were dissolved/suspended in DMSO (400 mL) and treated with NaOMe (537 mg, 9.94 mmol). The mixture was allowed to stir at room temperature for 2 hours to completion by TLC analysis of the crude. The reaction was poured into ice-cold water (700 mL; white emulsion) and neutralized with the addition of 1M HCl solution. The aqueous portion was extracted with ethyl acetate (3×), and the organics were combined. The organic portion was washed with water twice, once with brine, separated, dried over MgSO4, filtered, and concentrated in vacuo to afford the crude product as a yellow oil. The residue was loaded onto a large fitted filtered with silica gel and eluted with 9:1 hexanes:ethyl acetate until the starting material/olefin were collected. The plug was then eluted with 1:1 hexanes:ethyl acetate until the pure desired product was eluted completely. The concentrated pure fractions yielded methyl 2-(4-chlorophenyl)-3-hydroxypropanoate as a colorless oil (39.4 g, 92%).

1. extractionThe aqueous portion was extracted with ethyl acetate (3×)
2. washThe organic portion was washed with water twice
3. customonce with brine, separated
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto afford the crude product as a yellow oil
8. customa large fitted
9. filtrationfiltered with silica gel
10. washeluted with 9:1 hexanes
11. customethyl acetate until the starting material/olefin were collected
12. washThe plug was then eluted with 1:1 hexanes
13. washethyl acetate until the pure desired product was eluted completely