Nitric Acid → Butyric Acid

Participants

Reaction Steps

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).

Provenance & Evidence