Reaktion #5354

Reaktionsgleichung

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

water

KOH

→

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

Ausbeute 103.7%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted three times with diethyl ether
2. 2
   Extraktionextracted three times with diethyl ether
3. 3
   Waschenwashed with brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigeto give a yellow oil
8. 8
   SonstigeThe residue is purified via flash chromatography on a 40 mm×150 mm silica column
9. 9
   Wascheneluting with 40% ethyl acetate/hexane

Vorschrift

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.

Quelle