O-Methylhydroxylamine → Methyl alpha-[2-methyl-4-(2-methoxyiminoethyl)-phenyloxymethylphenyl]-beta-methylacrylate
Reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([C:16](=O)[CH3:17])[CH:5]=[CH:4][C:3]=1[C:19](=[CH:24][CH3:25])[C:20]([O:22][CH3:23])=[O:21].[CH3:26][O:27][NH2:28]>CO>[CH3:1][C:2]1[C:7]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([CH2:16][CH:17]=[N:28][O:27][CH3:26])[CH:5]=[CH:4][C:3]=1[C:19](=[CH:24][CH3:25])[C:20]([O:22][CH3:23])=[O:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
22 g (67.4 mmol) of methyl α-[2-methyl-4-acetylphenyloxymethylphenyl]-β-methylacrylate and 11.3 g (0.135 mol) of O-methylhydroxylamine hydrochloric were refluxed in 600 ml of methanol for 6 hours. The mixture was allowed to cool to about 25° C., was hydrolyzed and extracted with ice water. The organic phases were washed with water, dried and evaporated down. There was obtained 18 g of the title compound in the form of pale yellow crystals (mp.: 55°-60° C.).
Workup
- extractionextracted with ice water
- washThe organic phases were washed with water
- customdried
- customevaporated down
Sources & evidence
- ORD record
- ord-5e70d0040c7e40859f93a0c83a6c18f8
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05298527
Reaction notes
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