반응 #5354

반응 방정식

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

water

KOH

→

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

수율 103.7%

용매

methanol

반응 조건

후처리

1. 1
   추출extracted three times with diethyl ether
2. 2
   추출extracted three times with diethyl ether
3. 3
   세척washed with brine
4. 4
   건조dried over Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타to give a yellow oil
8. 8
   기타The residue is purified via flash chromatography on a 40 mm×150 mm silica column
9. 9
   세척eluting with 40% ethyl acetate/hexane

실험 절차

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.

출처