O-Xylene → HCID 23720265, compound

HRID 1755770Notes

Reaction equation

HRID 1755770 reaction equation
C1(C)C(C)=CC=CC=1.[CH:9]1[CH:14]=[C:13]([OH:15])[C:12]([S:16]([O-:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1.[Na+:20].[C:21]1(=[O:35])[N:25]([CH2:26][C:27](Cl)=[O:28])[C:24](=[O:30])[C:23]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:22]12>CC(C)=O>[C:24]1(=[O:30])[N:25]([CH2:26][C:27]([O:15][C:13]2[CH:14]=[CH:9][CH:10]=[CH:11][C:12]=2[S:16]([O-:19])(=[O:17])=[O:18])=[O:28])[C:21](=[O:35])[C:22]2=[CH:34][CH:33]=[CH:32][CH:31]=[C:23]12.[Na+:20]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 23674503Sodium o-phenolsulfonate

Product 1

HCID 23720265HCID 23720265, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

500 g of xylene are added to 98.0 g (0.5 mol) of anhydrous sodium phenolsulfonate and 112.0 g (0.5 mol) of α-phthalimidoacetyl chloride and the mixture is kept at 140° C. for 15 hours. After cooling, the reaction mixture is taken up in acetone, the solvent is filtered off with suction over a Buchner funnel and the crystal sludge is washed twice more with 80 ml of acetone each time. After recrystallization from 90% strength ethanol, the resulting product is dried at 40° C. under a water pump vacuum.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solvent is filtered off with suction over a Buchner funnel
  3. washthe crystal sludge is washed twice more with 80 ml of acetone each time
  4. customAfter recrystallization from 90% strength ethanol
  5. customthe resulting product is dried at 40° C. under a water pump vacuum

Sources & evidence

ORD record
ord-5ac713de787d42b4b70c495e2a7b9a9b
Source dataset
uspto-grants-1995_08
Patent number
US05438147

Reaction notes

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