Methyl 3-cyano-4-methoxybenzoate → 3-Cyano-4-hydroxybenzoic acid

HRID 2109385Notes

Reaction equation

HRID 2109385 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13]C)[C:6]([O:8]C)=[O:7])#[N:2].Cl.N1C=CC=CC=1>>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([OH:8])=[O:7])#[N:2]

Participants

3

Reactant 2

HCID 2801011Methyl 3-cyano-4-methoxybenzoateHCID 10176127Pyridinium chloride

Product 1

HCID 111374633-Cyano-4-hydroxybenzoic acidYield 80.5%

Conditions

Temperature
180 °C

Procedure

A mixture of methyl 3-cyano-4-methoxybenzoate (70 g) and pyridine hydrochloride (128.3 g) was stirred for 1 hour at 180° C. in an oil bath. Ice-water (1 L) was added to the reaction mixture, and the thus-precipitated crystals were filtered and recrystallized from ethyl acetate, thereby giving 48.1 g of the desired compound.

Workup

  1. filtrationthe thus-precipitated crystals were filtered
  2. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-297cf8eef7004665a24d50ded460c15a
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

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