3-Amino-4-methylbenzonitrile → 3-Hydroxy-4-methylbenzonitrile

HRID 2184231Notes

Reaction equation

HRID 2184231 reaction equation
N([O-])=[O:2].[Na+].N[C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:9]#[N:10]>O.Cl>[OH:2][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:9]#[N:10]

Participants

5

Reactant 2

HCID 70164283-Amino-4-methylbenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 177509203-Hydroxy-4-methylbenzonitrileYield 43%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of 49.2 g (0.72 mol) of NaNO2 in 217 ml of water was added dropwise over the course of 30 min to 85 g (0.72 mol) of 3-amino-4-methylbenzonitrile in 1.8 l of 6N HCl at 0-5° C. The mixture was then stirred at 0-5° C. for a further 30 min and then at the boiling point for 1 h. After the solution had cooled it was possible to extract the product with ethyl acetate and, from this, the phenolate with ice-cold 5N NaOH. The aqueous phase was then acidified to pH 3 with 6N HCl and the product was extracted with ethyl acetate. 41 g (43%) of the phenol were obtained. 1H-NMR (DMSO-d6; δ in ppm): 10.3 (s, OH); 7.25 (dd, 1H); 7.15 (d, 1H); 7.1 (dd, 1H); 2.20 (s, 3H)

Workup

  1. waitat the boiling point for 1 h
  2. temperatureAfter the solution had cooled it
  3. extractionto extract the product with ethyl acetate
  4. extractionthe product was extracted with ethyl acetate

Sources & evidence

ORD record
ord-48157474e0c24f0e96ea44df2b2da31b
Source dataset
uspto-grants-2005_05
Patent number
US06900319B2

Reaction notes

Loading…