Water → 1-[3-(3,4-Dichloro-benzyloxy)-phenyl]-ethanone

HRID 391817Notes

Reaction equation

HRID 391817 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:21]Cl.O>CN(C=O)C.[I-].[K+]>[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:21][O:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 76093,4-Dichlorobenzyl chlorideHCID 84873-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 288256531-[3-(3,4-Dichloro-benzyloxy)-phenyl]-ethanoneYield 72.8%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3′-hydroxyacetophenone (19 g) in DMF (400 mL) was added K2CO3 (38.5 g) and the mixture was stirred for 3 hours at room temperature. 3,4-Dichlorobenzyl chloride (32.7 g) and potassium iodide (1.16 g) were added to the reaction mixture and stirred for 48 hours. After completion of the reaction, the mixture was poured into ice and water mixture and stirred for 15 minutes, solid was filtered and washed with water and hexanes. Solid was dissolved in DCM and precipitated by adding hexanes to get pure 1-[3-(3,4-dichloro-benzyloxy)-phenyl]-ethanone (30 g) 1H NMR (400 MHz, CDCl3) 7.53-7.60 (m, 3H), 7.46 (d, 1H), 7.39 (t, 1H), 7.25-7.30 (m, 1H), 7.14-7.19 (m, 1H), 5.07 (s, 2H), 2.60 (s, 3H).

Workup

  1. stirringstirred for 48 hours
  2. customAfter completion of the reaction
  3. stirringstirred for 15 minutes
  4. filtrationsolid was filtered
  5. washwashed with water and hexanes
  6. dissolutionSolid was dissolved in DCM
  7. customprecipitated
  8. additionby adding hexanes

Sources & evidence

ORD record
ord-05442841197b405c9d7f30ffd5d5969c
Source dataset
uspto-grants-2013_02
Patent number
US08383644B2

Reaction notes

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