Water → 2-(4-Chlorophenoxy)-1-phenylethanone

HRID 1402916Notes

Reaction equation

HRID 1402916 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9](Br)[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 46844-ChlorophenolHCID 6259Phenacyl bromide

Product 1

HCID 3095712-(4-Chlorophenoxy)-1-phenylethanoneYield 98.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chlorophenol (0.774 g) and phenacyl bromide (1 g) in N,N-dimethyl formamide (10 ml) potassium carbonate (3.5 g) was added. The mixture was refluxed with stirring for 2 h. After cooling the reaction mixture was poured into water (50 ml) and extracted with dichloromethane (3×20 ml). The combined organic layers were washed with water (20 ml) and brine (20 ml), dried (MgSO4), and evaporated. The crude was purified by flash chromatography on silica gel (petrol ether/ethyl acetate 10:1) to give 2-(4-chlorophenoxy)-1-phenylethanone (1.22 g) as pale yellow solid.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureAfter cooling the reaction mixture
  3. extractionextracted with dichloromethane (3×20 ml)
  4. washThe combined organic layers were washed with water (20 ml) and brine (20 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude was purified by flash chromatography on silica gel (petrol ether/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-b85cb1ffd1544f7daad706748a3ac466
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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