Hydrochloric Acid → Methyl 3-cyano-4-hydroxybenzoate

HRID 234772Notes

Reaction equation

HRID 234772 reaction equation
C([O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:9][C:6]=1[C:7]#[N:8])(=O)C.C[O-].[Na+].Cl>CO>[OH:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:9][C:6]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 54012634Methyl 4-acetoxy-3-cyanobenzoate

Product 1

HCID 11769089Methyl 3-cyano-4-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 70.6 g (0.32 mol) of the compound from Example XXXVIII and 3.48 g (0.06 mol) of sodium methylate in 0.5 l of methanol is heated under reflux for 3 hours, the pH is brought to 6.5 with 1N hydrochloric acid at 25° C., the mixture is concentrated in vacuo, the residue is taken up in methylene chloride, the mixture is washed with saturated sodium chloride solution, the organic phase is dried over sodium sulphate and concentrated and the residue is crystallised from diethyl ether/petroleum ether mixtures.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. concentrationthe mixture is concentrated in vacuo
  4. washthe mixture is washed with saturated sodium chloride solution
  5. dry with materialthe organic phase is dried over sodium sulphate
  6. concentrationconcentrated
  7. customthe residue is crystallised from diethyl ether/petroleum ether mixtures

Sources & evidence

ORD record
ord-75a3756f8f974021a77189080b6634cf
Source dataset
uspto-grants-1997_01
Patent number
US05596006

Reaction notes

Loading…