Acetylresorcinol → HCID 86594026, compound

HRID 1352876Notes

Reaction equation

HRID 1352876 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Ca+2].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[O:11][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 5055AcetylresorcinolHCID 7748Ethyl bromoacetateHCID 10112Calcium Carbonate

Product 1

HCID 86594026HCID 86594026, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-acetoxyphenol (3.04 g, 20 ml) in dimethylformamide were added calcium carbonate (2.76 g, 20 mmol) and ethyl bromoacetate (2.2 ml, 20 mmol), and the mixture was stirred for 2 hours at room temperature. The reaction was quenched by water and the mixture was extracted with ethyl acetate. The organic layer was washed with water, 10% aqueous citric acid solution, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution, and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified with silica gel chromatography (hexane:ethyl acetate=10:1) to give ethyl [3-(acetyloxy)phenoxy]acetate (3.30 g, 69%).

Workup

  1. customThe reaction was quenched by water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water, 10% aqueous citric acid solution
  4. dry with materialan aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution, and dried over sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified with silica gel chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-ebba593b6ca146cdae0559ec018826d7
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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