Chemical Properties
White to beige crystalline powder
Uses
Intermediate in the preparation of HIV replication inhibitors.
Definition
ChEBI: 4-Hydroxy-3,5-dimethylbenzonitrile is a hydroxytoluene.
Flammability and Explosibility
Not classified
Synthesis
GENERAL STEPS: Under nitrogen protection, 4-bromo-2,6-dimethylphenol (0.250 mmol), malononitrile (0.500 mmol), palladium catalyst (0.005 mmol), CuI (0.125 mmol), 1,10-phenanthroline (0.063 mmol), t-BuONa (0.500 mmol) and KF ( 0.500 mmol) were dissolved in DMF or NMP (1 mL). The reaction mixture was stirred at 130 °C for 24 hours. After the reaction was completed, the reaction mixture was diluted with EtOAc (4.0 mL), filtered through the diatomite layer and the diatomite layer was washed with EtOAc. The filtrate and washings were combined and concentrated under reduced pressure to remove the solvent to give the crude product. The reaction conversion was determined by GC analysis. The crude product was purified by silica gel column chromatography to give pure 3,5-dimethyl-4-hydroxybenzonitrile.
References
[1] Synlett, 2014, vol. 25, # 4, p. 547 - 550
