Water → 2,6-Bis-benzyloxybenzoic Acid Benzyl Ester

HRID 660617

Reaction equation

HRID 660617 reaction equation
O[C:2]1[CH:10]=[CH:9][CH:8]=[C:7](O)[C:3]=1[C:4](O)=[O:5].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20]([O-:23])([O-])=[O:21].[K+].[K+].[OH2:26]>CN(C=O)C>[CH2:12]([O:23][C:20](=[O:21])[C:2]1[C:10]([O:26][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=[CH:7][C:3]=1[O:5][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 93382,6-Dihydroxybenzoic AcidHCID 11430Potassium Carbonate

Product 1

HCID 145620262,6-Bis-benzyloxybenzoic Acid Benzyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-dihydroxybenzoic acid (1.54 g, 10 mmol) and benzyl bromide (3.63 mL, 30.5 mmol) in DMF (20 mL) is added K2CO3 (4.83 g, 30.5 mmol) and the mixture is stirred at RT for 48 h. Water is added and the mixture is extracted with EtOAc. The organic phase is washed with water and brine then is dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using hexane/EtOAc (8:1) as eluent to give the title compound.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. washThe organic phase is washed with water and brine
  3. dry with materialthen is dried over sodium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-a81e8126fd804bb4b76982e317e953de
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Linked notes

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