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Water → Methyl 10-(2-methoxy-5-methylphenyl)-10-oxo-decanoate

HRID 228688
Notes
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Reaction equation

HRID 228688 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.Cl([O-])(=O)(=O)=O.[Li+].Cl[C:17](=[O:30])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27].O>[N+](C)([O-])=O.[O-]S(C(F)(F)F)(=O)=O.[Sc+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=1[C:17](=[O:30])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 77314-MethylanisoleHCID 544219Methyl 10-chloro-10-oxodecanoateHCID 23665649Lithium perchlorate

Product 1

HCID 23078595Methyl 10-(2-methoxy-5-methylphenyl)-10-oxo-decanoateYield 83%

Reagents, catalysts & solvents 2

HCID 2734571
Scandium(III) triflate
Catalyst
HCID 6375NitromethaneSolvent

Procedure

4-Methylanisole (732 mg) was dissolved in nitromethane (30 ml) to prepare a solution. Anhydrous lithium perchlorate (3.8 g), methyl 10-chloro-10-oxodecanoate (2 ml), and scandium triflate (300 mg) were added to the solution, and the mixture was stirred at room temperature for 4 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give methyl 10-(2-methoxy-5-methylphenyl)-10-oxo-decanoate (1.6 g, yield 83%).

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3f17d85902ba4e73828d1a076a677354
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07560558B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes