Water → HCID 21287217, compound

HRID 868531Notes

Reaction equation

HRID 868531 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[C:11](=[O:14])([O-])[O-].[K+].[K+].[Cl:17][C:18]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:19]=1CCl.O>CS(C)=O>[Cl:17][C:18]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:19]=1[CH2:11][O:14][CH2:9][C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1)=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 72122,4-Dichlorobenzyl chlorideHCID 83752'-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 21287217HCID 21287217, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

o-Hydroxyacetophenone (40.85 g, 300 mmole) was dissolved in dimethyl sulfoxide (150 ml) and potassium carbonate (49.0 g, 355 mmole) was added to the mixture. Then, 2,4-dichlorobenzyl chloride (65.9 g, 337 mmole) was added dropwise with stirring. Stirring was continued at room temperature for 24 hours and water (225 ml) was added dropwise over 1 hour. After stirring at room temperature for additional 1 hour, the precipitated crystals were filtered off, washed with water (200 ml×3) and recrystallized from methanol to obtain the title compound (82.7 g, 93.4%), m.p. 83°-85° C.

Workup

  1. stirringStirring
  2. stirringAfter stirring at room temperature for additional 1 hour
  3. filtrationthe precipitated crystals were filtered off
  4. washwashed with water (200 ml×3)
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-dc3859f77853450cb071c0f381296a8d
Source dataset
uspto-grants-1988_10
Patent number
US04780471

Reaction notes

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