4-Hydroxybenzaldehyde → Ethyl 2-(4-formylphenoxy)acetate

HRID 1604527Notes

Reaction equation

HRID 1604527 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].O>CN(C)C=O>[CH2:21]([O:20][C:18]([CH2:17][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)=[O:19])[CH3:22]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 291358Ethyl 2-(4-formylphenoxy)acetateYield 93.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxybenzaldehyde (10 g) and potassium carbonate (17 g) in dimethylformamide (100 ml) was added ethyl bromoacetate (15 g) under ice-cooling, and the mixture was stirred for 2 hours at ambient temperature. Water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography (ethyl acetate:n-hexane, 1:4, V/V) to give 4-(ethoxycarbonylmethoxy)benzaldehyde (16 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (ethyl acetate:n-hexane, 1:4, V/V)

Sources & evidence

ORD record
ord-e4a8cbd5484248478a88aa2f39ccef09
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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