反応 #156587

反応方程式

4-butoxybenzoic acid

N,N,N′,N′-tetramethylethylenediamine

methyl iodide

sec-butyllithium

→

4-Butoxy-2-methylbenzoic acid

溶媒

water

THF

THF

反応条件

後処理

1. 1
   温度the mixture was warmed to −78° C.
2. 2
   温度to warm to room temperature
3. 3
   抽出extracted with ethyl acetate
4. 4
   乾燥The organic phase was dried over magnesium sulfate
5. 5
   濃縮concentrated
6. 6
   その他The residue was purified by chromatography on silica gel
7. 7
   その他The product with the molecular weight of 208.26 (C12H16O3) was obtained in this way

実験手順

A mixture of 4-butoxybenzoic acid (10 g), N,N,N′,N′-tetramethylethylenediamine (13.2 g) and THF (75 mL) was cooled to −90° C., and sec-butyllithium (81 mL; 1.4 M in hexane) was added over the course of 30 minutes. After a further 30 minutes, the mixture was warmed to −78° C., and a solution of methyl iodide (12.8 mL) in THF (10 mL) was added dropwise. The reaction solution was allowed to warm to room temperature and the mixture was hydrolyzed with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel. The product with the molecular weight of 208.26 (C12H16O3) was obtained in this way; MS (ESI): 209 (M+H+).

出典