Potassium Carbonate → Methyl 4-(2-oxopropoxy)phenylacetate

HRID 1901192Notes

Reaction equation

HRID 1901192 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.Br[CH2:14][C:15](=[O:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:17]=[C:15]([CH3:16])[CH2:14][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11715BromoacetoneHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 21832178Methyl 4-(2-oxopropoxy)phenylacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture comprising 74.6 g of methyl 4-hydroxyphenylacetate, 92.2 g of bromoacetone, 125 g of potassium carbonate and 750 ml of dimethylformamide was stirred at room temperature for 1 day. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure. The resulting concentrate was mixed with water and then extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate; the solvent was then removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:8 by volume mixture of ethyl acetate and benzene as the eluent, to give the title compound having an Rf=0.43 (thin layer chromatography over silica gel, using a 1:7 by volume mixture of ethyl acetate and benzene as the developing solvent).

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. concentrationThe resulting concentrate
  3. additionwas mixed with water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with an aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was then removed by distillation under reduced pressure
  8. customThe residue was purified by column chromatography through silica gel
  9. additionby volume mixture of ethyl acetate and benzene as the eluent

Sources & evidence

ORD record
ord-43274c45c06049b9b63c9b35f4a9cb2f
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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