Hydrochloric Acid → HCID 14798601, compound

Participants

Reaction Conditions

Reaction Steps

& B. A mixture of 100 g (0.74 mole) of 4-isopropylaniline (Aldrich Chemical Co.), 100 ml of water, and 200 ml of concentrated hydrochloric acid, was cooled at 5° C. and treated dropwise with a solution of 52 g (0.75 mole) of sodium nitrite in 150 ml of water. The mixture was kept at 5° C. for 1 hour. A solution of 90 g (0.94 mole) of furfural in 150 ml of acetonitrile was added all at once followed by a solution of 30 g of CuCl2.×H2O in 125 ml of water. The reaction mixture was stirred overnight at ambient temperature. The reaction mixture was warmed at 45° C. for 30 minutes and then cooled, and extracted with ether (3×400 ml). The combined ethereal extracts were washed with water (3×200 ml), saturated NaHCO3 solution (2×200 ml) and water (2×200 ml). The ethereal extract was dried over MgSOr and the solvent removed in vacuo (water pump). The residual oil was distilled under high vacuum using a flame. The product, 5-[4-(1-methylethyl)phenyl]-2-furancarboxaldehyde (B), was obtained as an oil (26 g, 16% yield); b.p. 160-175° C./0.5 mm Hg.

Provenance & Evidence