4'-Hydroxyacetophenone → HCID 18918397, compound

HRID 1940384Notes

Reaction equation

HRID 1940384 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>CN(C=O)C>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 18918397HCID 18918397, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of p-acetylphenol (10 g) in DMF (50 ml) were added potassium carbonate (12.2 g) and t-butyl bromoacetate (16.2 ml), and the mixture was stirred at room temperature for 2 hours. After the reaction mixture was concentrated under reduced pressure, the residue was diluted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. After the solvents were removed by distillation, crystals thus obtained were washed with n-hexane to give 17.7 g of t-butyl 4-acetylphenoxyacetate (yield, 96%).

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the solvents were removed by distillation, crystals
  6. customthus obtained
  7. washwere washed with n-hexane

Sources & evidence

ORD record
ord-051ef81582674ad49ca9795008f8a723
Source dataset
uspto-grants-1997_12
Patent number
US05698692

Reaction notes

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