反応 #362621

反応方程式

m-fluorophenol

methyl 2-chloropropionate

HCl

→

2-(3' -fluorophenoxy)propionic acid

収率 42.0%

溶媒

sodium hydroxide

反応条件

後処理

1. 1
   温度to cool
2. 2
   その他reached about 40° C.
3. 3
   温度to cool to room temperature
4. 4
   抽出The reaction mixture was extracted twice with 100 ml ethyl ether
5. 5
   洗浄washed with 200 ml of 1.5M aqueous sodium carbonate
6. 6
   その他The aqueous layer was separated
7. 7
   workup.ADDITIONby adding concentrated HCl
8. 8
   抽出The acidified aqueous layer was extracted with 200 ml ethyl ether
9. 9
   その他The organic layer was separated
10. 10
    乾燥dried with MgSO4
11. 11
    ろ過filtered
12. 12
    その他The solvent was removed in vacuo

実験手順

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.).

出典