4'-Hydroxyacetophenone → 1-[4-(2-Chloroethoxy)phenyl]ethanone

HRID 1366356Notes

Reaction equation

HRID 1366356 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][Cl:14].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:14][CH2:13][CH2:12][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium Carbonate

Product 1

HCID 136911911-[4-(2-Chloroethoxy)phenyl]ethanoneYield 99.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4′-hydroxyacetophenone (101 g, 0.74 mole) in acetone (800 mL) was added 1-bromo-2-chloroethane (638 g, 4.45 mole) followed by K2CO3 (307 g, 2.22 mole). The reaction was heated to reflux for 48 h then filtered. The K2CO3 was washed with acetone (1 L) and the filtrate was evaporated. The residue was then partitioned between EtOAc (800 mL) and 1 N NaOH (250 mL). The organic layer was washed with 1 N NaOH (250 mL) then dried and evaporated to yield 146 g of the desired product (99% yield).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 48 h
  3. filtrationthen filtered
  4. washThe K2CO3 was washed with acetone (1 L)
  5. customthe filtrate was evaporated
  6. customThe residue was then partitioned between EtOAc (800 mL) and 1 N NaOH (250 mL)
  7. washThe organic layer was washed with 1 N NaOH (250 mL)
  8. customthen dried
  9. customevaporated

Sources & evidence

ORD record
ord-ddb60aef56ae447ea064d50710562dc0
Source dataset
uspto-grants-2011_02
Patent number
US07893057B2

Reaction notes

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