2,6-Dimethoxybenzonitrile → 2,6-Dihydroxybenzonitrile

HRID 2282067Notes

Reaction equation

HRID 2282067 reaction equation
Cl.N1C=CC=CC=1.C[O:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18]C)[C:11]=1[C:12]#[N:13]>O>[OH:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:11]=1[C:12]#[N:13]

Participants

4

Reactant 2

HCID 856482,6-DimethoxybenzonitrileHCID 10176127Pyridinium chloride2×

Product 1

HCID 937912,6-DihydroxybenzonitrileYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
210 °C

Procedure

Another potential method utilizes pyridine hydrochloride in place of the boron tribromide. Into a 500 mL 3-neck round bottom flask equipped with stir bar, nitrogen inlet and condenser was charged 2,6-dimethoxybenzonitrile (15.0 g, 91.9 mmol), followed by pyridine hydrochloride (150 g). The mixture was heated to 210° C. for 2 hours and allowed to cool to room temperature. Water was then added to the flask to dissolve the solidified mixture. The aqueous layer was then extracted with ethyl acetate (150 mL) 3 times. The combined organic layer was dried under anhydrous sodium sulfate, and the solvent was removed to yield 7.44 g (60.0%) of a light pink solid, m.p.: 202.8-204.8° C. 1H-NMR (DMSO-d6): 6.39-6.41 (d, 2H, Ar—H), 7.20-7.24 (t, 1H), 10.78 (s, 2H, Ar—O—H).

Workup

  1. customInto a 500 mL 3-neck round bottom flask equipped
  2. temperatureto cool to room temperature
  3. dissolutionto dissolve the solidified mixture
  4. extractionThe aqueous layer was then extracted with ethyl acetate (150 mL) 3 times
  5. customThe combined organic layer was dried under anhydrous sodium sulfate
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-d896ef3866aa493dbffc2253c29e1818
Source dataset
uspto-grants-2015_09
Patent number
US09139696B1

Reaction notes

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