3-Hydroxybenzyl alcohol → [3-(2-Methoxyethoxy)phenyl]methanol

HRID 2242356Notes

Reaction equation

HRID 2242356 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].Br[CH2:11][CH2:12][O:13][CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH3:14][O:13][CH2:12][CH2:11][O:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 20110194[3-(2-Methoxyethoxy)phenyl]methanolYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Hydroxybenzyl alcohol (3.76 g, 30 mmol), 2-bromoethylmethyl ether (8.0 ml, 85 mmol) and cesium carbonate (14.7 g, 45 mmol) were heated at 60° C. for 3 h. The reaction was diluted with water, extracted (3×) with ethyl acetate and dried over sodium sulfate. The solution was filtered, concentrated and purified by silica chromatography (DCM followed by DCM/MeOH 19:1, then 9:1) to yield [3-(2-methoxyethoxy)phenyl]methanol as an orange oil (3.92 g, 72%).

Workup

  1. extractionextracted (3×) with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationThe solution was filtered
  4. concentrationconcentrated
  5. custompurified by silica chromatography (DCM

Sources & evidence

ORD record
ord-450e93d85bbb42069caf47beb2dc3c0e
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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