Hydroxyamine hydrochloride → Methyl {4-[(hydroxyimino)methyl]phenoxy}acetate

HRID 902770Notes

Reaction equation

HRID 902770 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=O)=[CH:8][CH:7]=1.Cl.[OH:16][NH2:17].C([O-])(=O)C.[Na+]>CO.O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[N:17][OH:16])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 758214Methyl 2-(4-formylphenoxy)acetate

Product 1

HCID 73461790Methyl {4-[(hydroxyimino)methyl]phenoxy}acetateYield 74.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of methyl-(4-formylphenoxy)acetate (100 g, 0.515 mol) in methanol (500 mL) was cooled to 0-5° C. To this was added a solution of hydroxyamine hydrochloride (54 g) and sodium acetate (64 g) in water (500 mL) drop-wise and stirred at rt for 6 h. The reaction mixture diluted with water and filtered off the solid. The solid was washed with water and dried under vacuum to give the title compound (80 g, 74%).

Workup

  1. filtrationfiltered off the solid
  2. washThe solid was washed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-74131beee52e4bfea4fdaa58938f437d
Source dataset
uspto-grants-2008_04
Patent number
US07365225B2

Reaction notes

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