Hydrochloric Acid → 4-Hydroxy-3-methylbenzonitrile

HRID 1003357Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([OH:8])=[CH:6][CH:7]=1.[Cu](C#N)[C:11]#[N:12].O.Cl>CN1C(=O)CCC1.C(OCC)(=O)C>[C:11]([C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([OH:8])=[CH:6][CH:7]=1)#[N:12]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixed solution of 10.89 g (58 mmol) of 4-bromo-cresol and 10.39 g (116 mmol) of copper cyanide in 50 ml of NMP was stirred at 190° C. for 2 hours, followed by the addition of 43 g of FeCl3.6H2O, 65 ml of water and 11 ml of concentrated hydrochloric acid. The resulting mixture was stirred at 80° C. for 30 minutes and was then allowed to cool down. Water and ethyl acetate were added to the reaction mixture, followed by separation into a water layer and an organic layer. The organic layer was dried over Na2SO4, and the solvent was then distilled off under reduced pressure. The residue as purified by column chromatography (chloroform/methanol=40/1), whereby 10.32 g of 4-cyanocresol were obtained as a dark brown oil.

Workup

temperatureto cool down
customfollowed by separation into a water layer
dry with materialThe organic layer was dried over Na2SO4
distillationthe solvent was then distilled off under reduced pressure
customThe residue as purified by column chromatography (chloroform/methanol=40/1)

Sources & evidence

ORD record: ord-38fb365d5a8b4d06abfc58fff0c22699
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06046212

Reaction notes

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