반응 #362621

반응 방정식

m-fluorophenol

methyl 2-chloropropionate

HCl

→

2-(3' -fluorophenoxy)propionic acid

수율 42.0%

용매

sodium hydroxide

반응 조건

후처리

1. 1
   온도to cool
2. 2
   기타reached about 40° C.
3. 3
   온도to cool to room temperature
4. 4
   추출The reaction mixture was extracted twice with 100 ml ethyl ether
5. 5
   세척washed with 200 ml of 1.5M aqueous sodium carbonate
6. 6
   기타The aqueous layer was separated
7. 7
   workup.ADDITIONby adding concentrated HCl
8. 8
   추출The acidified aqueous layer was extracted with 200 ml ethyl ether
9. 9
   기타The organic layer was separated
10. 10
    건조dried with MgSO4
11. 11
    여과filtered
12. 12
    기타The solvent was removed in vacuo

실험 절차

To a solution of m-fluorophenol (24.2 g, 0.22 mol) in 79.2 ml of 25% aqueous sodium hydroxide heated to 45° C. with an oil bath was added 29.5 ml (0.26 mol) methyl 2-chloropropionate. The reaction mixture was heated to 80° C. for 17 hours and then allowed to cool. When the temperature reached about 40° C., concentrated HCl (25 ml) was added and the reaction mixture was allowed to cool to room temperature. The reaction mixture was extracted twice with 100 ml ethyl ether. The organic layers were combined and washed with 200 ml of 1.5M aqueous sodium carbonate. The aqueous layer was separated and acidified to pH 1, by pH test paper, by adding concentrated HCl. The acidified aqueous layer was extracted with 200 ml ethyl ether. The organic layer was separated, dried with MgSO4 and filtered. The solvent was removed in vacuo to yield 17 g (41% yield) of 2-(3' -fluorophenoxy)propionic acid as a yellow solid (m.p. 72.5°-74° C.).

출처