4'-Hydroxypropiophenone → Ethyl 2-(4-propionylphenoxy)acetate

HRID 68305

Reaction equation

HRID 68305 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:18][CH2:19][O:20][C:21]([CH2:23]Br)=[O:22]>CN(C=O)C>[C:8]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:23][C:21]([O:20][CH2:19][CH3:18])=[O:22])=[CH:7][CH:6]=1)(=[O:11])[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 62714'-HydroxypropiophenoneHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 24693252Ethyl 2-(4-propionylphenoxy)acetateYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-hydroxyphenyl)propan-1-one (33 g, 0.2200 moles) in DMF (165 mL), potassium carbonate (60.7 gm, 0.4400 moles) and ethyl bromo acetate (40.6 gm, 0.2420 moles) were added and the reaction mixture was srirred at 50° C. for 3 hours. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evaporated under reduced pressure to yield 49 gm (94%) of product as thick liquid.

Workup

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. extractionThe combined ethyl acetate extract
  4. washwas washed with water & brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-563a30f967d248eba20cd06aba3ac5f5
Source dataset
uspto-grants-2014_09
Patent number
US08822414B2

Linked notes

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