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

HRID 708608Notes

Reaction equation

HRID 708608 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-af45f3a839004c2a9f72502ca1b034cd
Source dataset
uspto-grants-2015_11
Patent number
US09175003B2

Reaction notes

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