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

HRID 1492555Notes

Reaction equation

HRID 1492555 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][C:12]([OH:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].[CH3:21][C:22](C)=O>>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:11][C:12]([O:14][CH2:21][CH3:22])=[O:13])=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 180AcetoneHCID 6227Bromoacetic AcidHCID 11430Potassium Carbonate

Product 1

HCID 291358Ethyl 2-(4-formylphenoxy)acetate

Procedure

p-Hydroxybenzaldehyde (4.88 g), bromoacetic acid (6.68 g) and potassium carbonate (5.53 g) were suspended in 100 ml of acetone, and refluxed for 15 hours. After the solvent was distilled off under reduced pressure, water was added followed by extraction with methylene chloride. The organic phase was washed in saturated aqueous sodium chloride, and dried over magnesium sulfate. After distillation of the solvent under reduced pressure, 8.32 g of ethyl 4-formylphenoxyacetate was obtained.

Workup

  1. temperaturerefluxed for 15 hours
  2. distillationAfter the solvent was distilled off under reduced pressure, water
  3. additionwas added
  4. extractionfollowed by extraction with methylene chloride
  5. washThe organic phase was washed in saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. distillationAfter distillation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-d2cb29f612194fb1b1fc039a223d3422
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

Loading…