Water → 3-Formyl-4-hydroxybenzonitrile

Temperature

100 °C

To a solution of 4-cyanophenol (25.0 g) in trifluoroacetic acid (150 ml) was added hexamethylenetetramine (50.0 g) and the mixture was stirred at 100° C. for 9 hours. After cooling to room temperature, sulfuric acid (50 ml) and water (300 ml) were added to the reaction mixture. The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was extracted with dichloromethane. The extract was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by chromatography on a silica gel column using dichloromethane/ethyl acetate=19/1 as an eluant to give the desired compound (4.3 g, yield 13%) as a colorless solid.

1. temperatureAfter cooling to room temperature
2. stirringThe resulting mixture was stirred at room temperature for 1 hour
3. extractionThe reaction mixture was extracted with dichloromethane
4. washThe extract was washed with water and brine
5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationthe filtrate concentrated in vacuo
8. customThe residue was purified by chromatography on a silica gel column

ORD record

ord-20df9bc362ad4a618795c31cd17014e0

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06555556B1