Benzoic acid, 3-formyl-4-hydroxy-, methyl ester → 2-Hydroxy-5-methoxycarbonyl-benzaldehyde oxime

HRID 343966Notes

Reaction equation

HRID 343966 reaction equation
C([O-])(=O)C.[Na+].Cl.[NH2:7][OH:8].[OH:9][C:10]1[CH:17]=[CH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14][C:11]=1[CH:12]=O>O.CO>[OH:9][C:10]1[CH:17]=[CH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14][C:11]=1[CH:12]=[N:7][OH:8]

Participants

6

Reactant 3

HCID 212595Benzoic acid, 3-formyl-4-hydroxy-, methyl esterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 1363810712-Hydroxy-5-methoxycarbonyl-benzaldehyde oximeYield 80.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 68.0 g (0.83 mol) of sodium acetate and 68.0 g (0.98 mol) of hydroxylamine hydrochloride in 300 ml of water is added dropwise to a solution of 80.5 g (0.45 mol) of 2-hydroxy-5-methoxycarbonylbenzaldehyde in 300 ml of methanol and the mixture is stirred at 25° C. for 2 hours. The product which has precipitated is filtered off with suction, washed with water and dried in vacuo over phosphorus pentoxide to give 70.4 g of the title compound.

Workup

  1. customThe product which has precipitated
  2. filtrationis filtered off with suction
  3. washwashed with water
  4. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-61a27badf143493ea8ccb6f802de9946
Source dataset
uspto-grants-1999_01
Patent number
US05863930

Reaction notes

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