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O-Methylhydroxylamine hydrochloride → Methyl alpha-[2-methyl-4-(2-methoxyiminoethyl)-phenyloxymethylphenyl]-beta-methylacrylate

HRID 36609
Notes
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Reaction equation

HRID 36609 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].Cl.[CH3:27][O:28][NH2:29]>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:29][O:28][CH3:27])[CH:5]=[CH:4][C:3]=1[C:19](=[CH:24][CH3:25])[C:20]([O:22][CH3:23])=[O:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 86747704Methyl alpha-[2-methyl-4-acetylphenyloxymethylphenyl]-beta-methylacrylate

Product 1

HCID 86747703Methyl alpha-[2-methyl-4-(2-methoxyiminoethyl)-phenyloxymethylphenyl]-beta-methylacrylateYield 72.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 hydrochloride 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 (m.p.: 55°-60° C.).

Workup

  1. extractionextracted with ice water
  2. washThe organic phases were washed with water
  3. customdried
  4. customevaporated down

Sources & evidence

ORD record
ord-c2720426254a46cdad712ba06ca6465a
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05416068

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes