Hydrochloric Acid → 3-Hydroxy-4-methylbenzonitrile

HRID 1294448Notes

Reaction equation

HRID 1294448 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:5](N)[CH:4]=1)#[N:2].Cl.N([O-])=[O:13].[Na+].C1(C)C=CC=CC=1>O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:5]([OH:13])[CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 70164283-Amino-4-methylbenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 177509203-Hydroxy-4-methylbenzonitrileYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a reaction vessel was charged 4-cyano-2-aminotoluene (13) (132.0 g, 1.0 mol) and 6 N hydrochloric acid aqueous solution (800 ml), and an aqueous solution obtained by dissolving ice-cooled sodium nitrite (76.0 g, 1.1 mol) in water (320 ml) was dropped over 1.5 hours, further, the solution was stirred for approximately 20 hours under ref lux. To the reaction liquid was added toluene and extracted, then, a sodium hydroxide aqueous solution was added to the toluene layer to make the aqueous layer alkaline. The resulted aqueous layer was acidified with concentrated hydrochloric acid, then, extracted with ethyl acetate. The resulted ethyl acetate layer was washed with saturated saline, dried, and the solvent was distilled off under reduced pressure, to obtain 4-cyano-2-hydroxytoluene (14) (91.6 g, yield from (13) is 69%).

Workup

  1. customan aqueous solution obtained
  2. dissolutionby dissolving ice-
  3. additionwas dropped over 1.5 hours
  4. customTo the reaction liquid
  5. extractionextracted
  6. additiona sodium hydroxide aqueous solution was added to the toluene layer
  7. extractionextracted with ethyl acetate
  8. washThe resulted ethyl acetate layer was washed with saturated saline
  9. customdried
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2b3d0ebec3844ce09e8d8cc27afa9dc8
Source dataset
uspto-grants-2007_07
Patent number
US07241625B2

Reaction notes

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