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

HRID 743014Notes

Reaction equation

HRID 743014 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Isobutyl 2-acetyloxy-5-[2-(4-sulfophenyl)ethenyl]benzoate potassium salt (36.1 g, 0.08 mot) 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%).

Workup

  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

Sources & evidence

ORD record
ord-68aa3d13bd3244a4b13e1e3d18b7b913
Source dataset
uspto-grants-1996_09
Patent number
US05556855

Reaction notes

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