Water → N-methoxycarbonyl-3-(2-trans-butenyl)oxy-4-methoxyaniline

HRID 1090122Notes

Reaction equation

HRID 1090122 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([OH:14])[CH:7]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Cl)/[CH:22]=[CH:23]/[CH3:24].O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14]/[CH:21]=[CH:22]/[CH2:23][CH3:24])[CH:7]=1)=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 637923(2E)-1-Chloro-2-buteneHCID 15675233HCID 15675233, compound

Product 1

HCID 86745378N-methoxycarbonyl-3-(2-trans-butenyl)oxy-4-methoxyanilineYield 91.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The N-methoxycarbonyl-3-hydroxy-4-methoxyaniline (34.0 g) was dissolved in dimethylformamide (200 ml). Potassium carbonate (29.0 g) and trans-crotyl chloride (32.2 g) were added to the solution, and the mixture was stirred at room temperature for 5 hours. Water was added to the reaction mixture, and extraction was carried out with ethyl acetate. The extract was washed with saturated saline and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The crude crystal thus obtained was recrystallized from ethyl acetate-n-hexane to obtain N-methoxycarbonyl-3-(2-trans-butenyl)oxy-4-methoxyaniline (39.5 g).

Workup

  1. washThe extract was washed with saturated saline
  2. dry with materialdried over sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe crude crystal thus obtained
  5. customwas recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-0e0f9253ae06473b996fea191fd901bd
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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