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Potassium Carbonate → HCID 54080301, compound

HRID 1352878
Notes
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Reaction equation

HRID 1352878 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>O1CCCC1>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[O:11][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 152273Phenol, 3-(2-hydroxyethoxy)-

Product 1

HCID 54080301HCID 54080301, compoundYield 246%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-hydroxyethoxy)phenol (864 mg, 5 mmol) in tetrahydrofuran (20 ml) were added potassium carbonate (967 mg, 7 mmol) and t-butyl bromoacetate (0.89 ml, 6 mmol), and the mixture was stirred for 2 hours at room temperature. The reaction was quenched by 10% aqueous citric acid solution 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. The organic layer was dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified with silica gel chromatography (hexane:ethyl acetate=3:1) to give the subject compound (3.30 g, 69%).

Workup

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

Sources & evidence

ORD record
ord-7f5a3a90157046ac82155f5dff90f0eb
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07220773B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes