Reaktion #822563

Reaktionsgleichung

methyl 4-(8,8-dimethyl-5-p-tolyl-7,8-dihydro-2-naphthylselanylethynyl)-2-hydroxybenzoate

sodium hydroxide

hydrochloric acid

→

4-(8,8-Dimethyl-5-p-tolyl-7,8-dihydro-2-naphthylselanylethynyl)-2-hydroxybenzoic acid

Ausbeute 61.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl ether
2. 2
   SonstigeThe residue obtained
3. 3
   Sonstigeis purified by chromatography (eluent: 7/3 heptane/ethyl acetate)
4. 4
   SonstigeAfter recrystallization from a heptane/ethyl ether mixture
5. 5
   Sonstigea white solid is obtained (0.65 g; yield=61%; m.p.=201° C.)

Vorschrift

1.1 g (2 mmol) of methyl 4-(8,8-dimethyl-5-p-tolyl-7,8-dihydro-2-naphthylselanylethynyl)-2-hydroxybenzoate (described in Example 5b) are dissolved in 10 ml of tetrahydrofuran, and 0.96 g (24 mmol) of sodium hydroxide is then added. The reaction medium is heated at 100° C. for 14 hours, acidified with 2N hydrochloric acid solution and then extracted with ethyl ether. The residue obtained is purified by chromatography (eluent: 7/3 heptane/ethyl acetate). After recrystallization from a heptane/ethyl ether mixture, a white solid is obtained (0.65 g; yield=61%; m.p.=201° C.).

Quelle