Water → methyl 2-(3-acetylphenoxymethyl)phenylglyoxylate O-methyloxime

HRID 374306Notes

Reaction equation

HRID 374306 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=1)=[O:3].[CH3:11][O:12][N:13]=[C:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25]Br)[C:15]([O:17][CH3:18])=[O:16].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:11][O:12][N:13]=[C:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][O:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([C:2](=[O:3])[CH3:1])[CH:9]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 84873-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 54028047Methyl 2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate

Product 1

HCID 54262751methyl 2-(3-acetylphenoxymethyl)phenylglyoxylate O-methyloximeYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.0 g (0.022 mol) of 3-hydroxyacetophenone and 6.0 g (0.021 mol) of methyl 2-bromomethylphenylglyoxylate O-methyloxime are dissolved in 30 ml of dimethylformamide, and 5.5 g (0.040 yol) of potassium carbonate are added. The mixture is stirred at room temperature for 24 hours, hydrolyzed with water and extracted with methyl tert-butyl ether. The organic phase is washed with water, dried and concentrated. 5.8 g (85%) of methyl 2-(3-acetylphenoxymethyl)phenylglyoxylate O-methyloxime are obtained as a colorless oil.

Workup

  1. extractionextracted with methyl tert-butyl ether
  2. washThe organic phase is washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ef1a86baefb541b0b7066bb94a39a966
Source dataset
uspto-grants-1992_11
Patent number
US05166399

Reaction notes

Loading…