Phenol → 2-Hydroxybenzonitrile

HRID 623242Notes

Reaction equation

HRID 623242 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S-][C:9]#[N:10].[B]>>[C:9]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[OH:7])#[N:10]

Participants

4

Reactant 3

HCID 996PhenolHCID 9322ThiocyanateHCID 5462311Boron2×

Product 1

HCID 119072-Hydroxybenzonitrile

Procedure

The phenol (II) is allowed to react with a thiocyanate in the presence of a boron trihalogenide to give an intermediate compound (IIIa), and the boron compound (IIIa) is then treated with a strong base to give a 2-cyanophenol (Ia). Alternatively, the 2-cyanophenol (Ia) can be prepared via the thiocarboxyimidic acid ester (IVa) by stepwise hydrolysis. Thus, IIIa is at first treated with a weak base to give IVa, which is then treated with a strong base to give the 2-cyanophenol (Ia).

Workup

  1. customto give an intermediate compound (IIIa)

Sources & evidence

ORD record
ord-ab49e52eaaca4add835fc3ec346006c3
Source dataset
uspto-grants-1988_09
Patent number
US04774331

Reaction notes

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