Ethylene Glycol → 2-(4-Nitrophenoxy)ethanol

HRID 1482710Notes

Reaction equation

HRID 1482710 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([OH:14])[CH2:12][OH:13].C(=O)([O-])[O-].[Cs+].[Cs+].CCCCCC.C(OCC)(=O)C>O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:13][CH2:12][CH2:11][OH:14])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 9590p-FluoronitrobenzeneHCID 10796Cesium carbonateHCID 21226206Ethyl acetate hexane

Product 1

HCID 853812-(4-Nitrophenoxy)ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

In a 250 ml, 3-neck RBF equipped with a magnetic stirrer, reflux condenser, calcium chloride guard tube, 1-fluoro-4-nitrobenzene (10.0 g), ethylene glycol (50 ml) and cesium carbonate (46.0 g) were added. The reaction mixture was heated to 80° C. for 30 minutes and the reaction was monitored on TLC using hexane:ethyl acetate (5:5) as mobile phase. After completion of the reaction, the reaction mixture was cooled to room temperature and poured into cold water. Solid precipitate was filtered out and washed with water. Solid material was dried under reduced pressure at 45° C. for 1 hr to give 10.7 g of 2-(4-nitrophenoxy)ethanol, which was used in the next step without further purification.

Workup

  1. customIn a 250 ml, 3-neck RBF equipped with a magnetic stirrer
  2. temperaturereflux condenser, calcium chloride guard tube
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was cooled to room temperature
  5. filtrationSolid precipitate was filtered out
  6. washwashed with water
  7. customSolid material was dried under reduced pressure at 45° C. for 1 hr

Sources & evidence

ORD record
ord-251ddac25213472a841106714c7dffa8
Source dataset
uspto-grants-2016_08
Patent number
US09415049B2

Reaction notes

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