Water → HCID 4779021, compound

HRID 910178Notes

Reaction equation

HRID 910178 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].Br[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[O:15]([CH2:14][CH2:13][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4133Methyl SalicylateHCID 11430Potassium CarbonateHCID 68526Benzene, (2-bromoethoxy)-

Product 1

HCID 4779021HCID 4779021, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl salicylate (1.377 g, 9.05 mmol) in N,N-dimethylformamide (14 ml) were added β-bromophenetole (1.876 g, 9.33 mmol) and potassium carbonate (1.509 g, 10.91 mmol), and the mixture was stirred at 80° C. for 1.5 hr. Water was added to the reaction mixture, and the precipitated crystals were collected by filtration and washed with water and hexane to give methyl 2-(2-phenoxyethoxy)benzoate (1.545 g, 5.67 mmol, yield 63%). This was dissolved in methanol (10 ml), 2N-aqueous sodium hydroxide solution (10 ml) was added at room temperature, and the mixture was stirred at 60° C. for 3.5 hr. The reaction mixture was concentrated under reduced pressure and neutralized with 2N-aqueous hydrochloric acid solution, and the mixture was extracted with ethyl acetate. The extract was dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give a carboxylic acid compound 2-(2-phenoxyethoxy)benzoic acid (1.407 g, 5.45 mmol, yield 96%).

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washwashed with water and hexane

Sources & evidence

ORD record
ord-3dcef099ea464e7e9d43d8f1c3726f67
Source dataset
uspto-grants-2011_09
Patent number
US08022072B2

Reaction notes

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