Potassium Carbonate → 4-Hydroxy-3-methylbenzonitrile

HRID 400592Notes

Reaction equation

HRID 400592 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][C:6]=1[CH3:13])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][C:6]=1[CH3:13]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 552203614-Cyano-2-methylphenyl acetate

Product 1

HCID 109645604-Hydroxy-3-methylbenzonitrileYield 78.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A stirred solution of 4-cyano-2-methylphenyl acetate (5.2 g, 29.7 mmol) in 75 mL of methanol was treated with a solution of potassium carbonate (30 mmol, 4.15 g) in 25 mL of water at room temperature. After 30 minutes, the mixture was concentrated in vacuo and treated with 1 N sulfuric acid. The resulting precipitate was filtered, washed with water, and dried to give 3.1 g of 4-hydroxy-3-methylbenzonitrile as a white solid (78% yield).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additiontreated with 1 N sulfuric acid
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-87c6b5bbd2404f0b9177c6f110a986e3
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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