Potassium Carbonate → HCID 54080301, compound
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]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- customThe reaction was quenched by 10% aqueous citric acid solution
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with water, 10% aqueous citric acid solution
- dry with materialThe organic layer was dried over sodium sulfate
- customThe solvent was removed under reduced pressure
- 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
- Patent number
- US07220773B2
Reaction notes
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