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Hydrochloric Acid → 4,4'-dimethoxybenzophenone O-(3-ethoxycarbonyl-2-oxopropyl)oxime

HRID 477073
Notes
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Reaction equation

HRID 477073 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7](=[N:16][OH:17])[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].Cl[CH2:27][C:28](=[O:35])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].Cl>CN(C)C=O>[CH2:33]([O:32][C:30]([CH2:29][C:28](=[O:35])[CH2:27][O:17][N:16]=[C:7]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:6]1[CH:18]=[CH:19][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:31])[CH3:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 69484Ethyl 4-chloroacetoacetateHCID 289718n-Hydroxy-1,1-bis(4-methoxyphenyl)methanimine2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 140527694,4'-dimethoxybenzophenone O-(3-ethoxycarbonyl-2-oxopropyl)oximeYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.57 g (0.01 mol) of the 4,4'-dimethoxybenzophenone oxime as obtained in (1) was dissolved in 5 ml of dimethylformamide and 1.2 g of potassium tert-butoxide was added thereto under ice cooling. The resulting mixture was stirred for ten minutes. Then 1.8 g of ethyl 4-chloroacetoacetate was added thereto and the obtained mixture was stirred at room temperature. After two hours, the reaction mixture was poured into diluted hydrochloric acid and extracted with ethanol. The crude product thus obtained was purified by silica gel chromatography to give 3.1 g of the title compound.

Workup

  1. stirringthe obtained mixture was stirred at room temperature
  2. extractionextracted with ethanol
  3. customThe crude product thus obtained
  4. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-fd79a38f5c194fae99b1730f42f960f5
Source dataset
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04886834

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes