Dimethylformamide → Isobutyl 2-acetyloxy-5-[2-(4-(chlorosulfonyl)phenyl)ethenyl]benzoate

HRID 1464173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1464173
[K].[C:2]([O:5][C:6]1[CH:18]=[CH:17][C:16]([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([OH:30])(=O)=[O:28])=[CH:23][CH:22]=2)=[CH:15][C:7]=1[C:8]([O:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[O:9])(=[O:4])[CH3:3].CN(C)C=O.S(Cl)([Cl:38])=O.[OH-].[Na+]>ClCCl.O>[C:2]([O:5][C:6]1[CH:18]=[CH:17][C:16]([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([Cl:38])(=[O:30])=[O:28])=[CH:23][CH:22]=2)=[CH:15][C:7]=1[C:8]([O:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[O:9])(=[O:4])[CH3:3]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 86747765Isobutyl 2-acetyloxy-5-[2(4-sulfophenyl)ethenyl]benzoate potassium salt

Produkt 1

HCID 53789228Isobutyl 2-acetyloxy-5-[2-(4-(chlorosulfonyl)phenyl)ethenyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Isobutyl 2-acetyloxy-5-[2(4-sulfophenyl)ethenyl]benzoate potassium salt (36.1 g, 0.08 mol) was suspended in dichloromethane. Dimethylformamide (20 ml) and thionyl chloride (20 ml) were added, and the mixture refluxed with stirring for 3 h. After cooling to room temperature, water (15 ml) was added. By careful addition of 5M sodium hydroxide, the pH of the aqueous phase was adjusted to about 7. The phases were separated and the organic phase washed with water. The solution was dried (MgSO4), treated with activated carbon and filtered. After evaporation of the solvent, the solid residue was recrystallized from a toluene and petroleum ether mixture. Yield 19.5 g (57%).

Aufarbeitung

  1. temperaturethe mixture refluxed
  2. customThe phases were separated
  3. washthe organic phase washed with water
  4. dry with materialThe solution was dried (MgSO4)
  5. additiontreated with activated carbon
  6. filtrationfiltered
  7. customAfter evaporation of the solvent
  8. customthe solid residue was recrystallized from a toluene and petroleum ether mixture

Quellen und Nachweise

ORD-Eintrag
ord-c6d226213fb24b3d9034e5722f2ee417
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05302718

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