1,2-Benzenedimethanol → (2-{[(Oxan-2-yl)oxy]methyl}phenyl)methanol

HRID 2222218Notes

Reaction equation

HRID 2222218 reaction equation
[C:1]1([CH2:9][OH:10])[C:2]([CH2:7][OH:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.C1(C)C=CC=CC=1.[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1>>[O:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[O:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH2:9][OH:10]

Participants

3

Reactant 2

HCID 691531,2-BenzenedimethanolHCID 131726862HCID 131726862, compound

Product 1

HCID 11345082(2-{[(Oxan-2-yl)oxy]methyl}phenyl)methanol

Conditions

Temperature
30 °C

Procedure

To a suspension of 1,2-benzenedimethanol (5 g, 36.19 mmol) in toluene/2,3-dihydropyran (206 ml/11 ml) at 30° C. was added 3.62 g Dowex (50WX2-100). The reaction stirred at 30° C. for 5 hours. The mixture was filtered to remove Dowex, then concentrated in vacuo and put on vacuum pump overnight w/stirring to remove 2,3-dihydropyran. The crude reaction product was purified by normal phase chromatography (20% EtOAc/hexanes—25% -30%) to give a clear liquid (5.72 g).

Workup

  1. filtrationThe mixture was filtered
  2. customto remove Dowex
  3. concentrationconcentrated in vacuo
  4. customput on vacuum pump overnight
  5. stirringw/stirring
  6. customto remove 2,3-dihydropyran
  7. customThe crude reaction product
  8. customwas purified by normal phase chromatography (20% EtOAc/hexanes—25% -30%)

Sources & evidence

ORD record
ord-5efb0848cc894ae4bff7dd5ca8354e4c
Source dataset
uspto-grants-2008_05
Patent number
US07371754B2

Reaction notes

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