Hydrochloric Acid → HCID 14798601, compound

Temperature

5 °C

& 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.

1. temperatureThe reaction mixture was warmed at 45° C. for 30 minutes
2. temperaturecooled
3. extractionextracted with ether (3×400 ml)
4. washThe combined ethereal extracts were washed with water (3×200 ml), saturated NaHCO3 solution (2×200 ml) and water (2×200 ml)
5. extractionThe ethereal extract
6. customwas dried over MgSOr
7. customthe solvent removed in vacuo (water pump)
8. distillationThe residual oil was distilled under high vacuum

ORD record

ord-1b82146679fa47bda4dd8f9f80300356

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04895867