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

HRID 353432Notes

Reaction equation

HRID 353432 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 1N NaOH (250 mL). The organic layer was washed with 1N NaOH (250 mL) then dried aid 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 1N NaOH (250 mL)
  7. washThe organic layer was washed with 1N NaOH (250 mL)
  8. customthen dried aid
  9. customevaporated

Sources & evidence

ORD record
ord-c2ccbc51df764a37804295fb6683a1d1
Source dataset
uspto-grants-2004_06
Patent number
US06753329B2

Reaction notes

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