反応 #5354

反応方程式

10-(4-chlorophenyl)-dec-9-enoic acid methyl ester

water

KOH

→

10-(4-chlorophenyl)dec-9-enoic acid

収率 103.7%

溶媒

methanol

反応条件

後処理

1. 1
   抽出extracted three times with diethyl ether
2. 2
   抽出extracted three times with diethyl ether
3. 3
   洗浄washed with brine
4. 4
   乾燥dried over Na2SO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated in vacuo
7. 7
   その他to give a yellow oil
8. 8
   その他The residue is purified via flash chromatography on a 40 mm×150 mm silica column
9. 9
   洗浄eluting with 40% ethyl acetate/hexane

実験手順

To a solution of 1.62 g of 10-(4-chlorophenyl)-dec-9-enoic acid methyl ester in 200 mL of 4:1 methanol:water is added 5.4 g of KOH. The solution is stirred for 2 hours and extracted three times with diethyl ether. The aqueous layer is acidified with concentrated hydrochloric acid, and extracted three times with diethyl ether. The organic layers are combined, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give a yellow oil. The residue is purified via flash chromatography on a 40 mm×150 mm silica column eluting with 40% ethyl acetate/hexane to give 1.6 g (100%) of pure 10-(4-chlorophenyl)dec-9-enoic acid as a mixture of E and Z isomers.

出典