Reaktion #44686

Reaktionsgleichung

6,7-dihydro-1-benzofuran-4(5H)-one

ethanol

→

1-Benzofuran-4-ol

Lösungsmittel

decalin

dodecene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe mixture is filtered off through CELITE (diatomaceous earth)
2. 2
   WaschenThe CELITE (diatomaceous earth) is washed twice with ethanol
3. 3
   Einengenthe filtrate is concentrated
4. 4
   workup.ADDITIONThe residue, which still contains decalin and dodecene, is mixed with petroleum ether
5. 5
   Temperaturcooled in an ice bath
6. 6
   SonstigeThe solvent is decanted off
7. 7
   Sonstigethe oil is purified by preparative HPLC

Vorschrift

3.76 g (27.6 mmol) of 6,7-dihydro-1-benzofuran-4(5H)-one (prepared according to Tetrahedron Lett. 1994, 35, 6231) and 10% of palladium on activated carbon in 34 ml of decalin and 6 ml of dodecene are heated in a metal bath at 200° C. overnight. The mixture is cooled to 80° C., ethanol is added and the mixture is filtered off through CELITE (diatomaceous earth). The CELITE (diatomaceous earth) is washed twice with ethanol and the filtrate is concentrated. The residue, which still contains decalin and dodecene, is mixed with petroleum ether and cooled in an ice bath. An oily precipitate forms. The solvent is decanted off and the oil is purified by preparative HPLC.

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