Ethylene Glycol → 2-[(3-Nitrophenyl)methoxy]ethanol

HRID 2116956Notes

Reaction equation

HRID 2116956 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].[N+:7]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH2:13]Br)([O-:9])=[O:8].P([O-])([O-])([O-])=O>CN(C=O)C.O>[N+:7]([C:10]1[CH:11]=[C:12]([CH2:13][O:3][CH2:2][CH2:1][OH:4])[CH:15]=[CH:16][CH:17]=1)([O-:9])=[O:8]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 1061PhosphateHCID 24758Sodium hydrideHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 121923882-[(3-Nitrophenyl)methoxy]ethanolYield 358%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethylene glycol (7.18 g) in anhydrous DMF (50 ml) was treated at 0° under nitrogen with sodium hydride (60% dispersion in mineral oil, 1.85 g) and the mixture stirred for 30 min. 3-Nitrobenzyl bromide (5.00 g) was added and the mixture was warmed to 200 over 1 h and stirred for a further 15 h. Phosphate buffer (pH 6.5, 100 ml) and water (100 ml) were added and the product was extracted with EtOAc (2×150 ml). The combined organic layer was washed with water (2×200 ml) and dried (Na2SO4). Solvent evaporation in vacuo gave a residue that was purified by Biotage. Elution with EtOAc-PE (1:1 then 2:1) followed by solvent evaporation in vacuo gave the title compound (16.34 g) HPLC RT=1.554 min. TSP+ve 215 (MNH4)+.

Workup

  1. temperaturethe mixture was warmed to 200 over 1 h
  2. stirringstirred for a further 15 h
  3. extractionthe product was extracted with EtOAc (2×150 ml)
  4. washThe combined organic layer was washed with water (2×200 ml)
  5. dry with materialdried (Na2SO4)
  6. customSolvent evaporation in vacuo
  7. customgave a residue that
  8. customwas purified by Biotage
  9. washElution with EtOAc-PE (1:1
  10. custom2:1) followed by solvent evaporation in vacuo

Sources & evidence

ORD record
ord-189335f993ae4a1b9f5b1f639638057c
Source dataset
uspto-grants-2008_10
Patent number
US07439393B2

Reaction notes

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