Reaktion #346163

Reaktionsgleichung

nitric acid

4-[4-(1-adamantyl)-phenoxy]-butyric acid

→

4-[2-nitro-4-(1-adamantyl)-phenoxy]-butyric acid

butyric acid

Lösungsmittel

acetic acid

acetic acid

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter completion of the addition
2. 2
   workup.STIRRINGthe mixture is stirred for a further 15 minutes at -5° C and 30 minutes at -3° C
3. 3
   Extraktionextracted with 3 times 200 ml of methylene chloride
4. 4
   WaschenThe organic phases are washed until neutral,
5. 5
   Trocknendried over sodium sulphate
6. 6
   Sonstigeevaporated in vacuo

Vorschrift

120 ml of fuming nitric acid in 40 ml of glacial acetic acid are added dropwise to a solution of 31.4 g of 4-[4-(1-adamantyl)-phenoxy]-butyric acid in 100 ml of glacial acetic acid and 30 ml of methylene chloride at -5° C, whilst stirring in an aqueous atmosphere. After completion of the addition, the mixture is stirred for a further 15 minutes at -5° C and 30 minutes at -3° C. The reaction mixture is then poured onto 1 kg of ice and extracted with 3 times 200 ml of methylene chloride. The organic phases are washed until neutral, dried over sodium sulphate and evaporated in vacuo. Chromatography of the evaporation residue on 1 kg of silica gel, with ethyl acetate as the eluant, gives 4-[2-nitro-4-(1-adamantyl)-phenoxy]-butyric acid of melting point 182°-185° C (from methylene chloride/petroleum ether) and 4-[2,6;l -dinistro- 4-(1-adamantyl)-phenoxy]-butyric acid of melting point 170°-172° C (from ethanol-pentane).

Quelle