Methyl 4-Formylbenzoate → Methyl 4-(hydroxyiminomethyl)benzoate

HRID 1525335Notes

Reaction equation

HRID 1525335 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+]>C1COCC1.O.ClCCl>[OH:15][N:14]=[CH:1][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 6804457Methyl 4-(hydroxyiminomethyl)benzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of methyl 4-formylbenzoate, 37-c, (5.0 g, 30.5 mmol) and hydroxylamine hydrochloride (2.5 g, 36.6 mmol) in THF/H2O (VTHF:VH2O=4:1, 50 mL) was added sodium acetate (3.5 g, 42.7 mmol). The reaction mixture was stirred at room temperature overnight and diluted with dichloromethane (400 mL), washed with water, dried with anhydrous Na2SO4, filtrated and concentrated in vacuo to provide compound, 37-d, (4.9 g, 90%).

Workup

  1. washwashed with water
  2. dry with materialdried with anhydrous Na2SO4
  3. filtrationfiltrated
  4. concentrationconcentrated in vacuo
  5. customto provide compound, 37-d, (4.9 g, 90%)

Sources & evidence

ORD record
ord-6f92a224460f4526b1bf848d85d535b3
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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