Ethylene Glycol → 2-(4-Nitrophenoxy)ethanol

HRID 1482694Notes

Reaction equation

HRID 1482694 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:17]([OH:20])[CH2:18][OH:19].CCCCCC.C(OCC)(=O)C>O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:19][CH2:18][CH2:17][OH:20])=[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

Into a 100 mL 3-neck RBF equipped with a magnetic stirrer, reflux condenser, and thermo pocket were added 4-fluoro nitrobenzene (5.00 g), Cs2CO3 (23.0 g) and ethylene glycol (50 mL). The reaction mixture was heated to 80° C. for 30 minutes. The reaction was monitored on TLC using hexane:ethyl acetate (7:3) as mobile phase. After completion, the reaction mixture was cooled to room temperature and poured into cold water. Solid precipitate was filtered and washed with water. Solid material was dried under reduced pressure at 45° C. for 1 hr to give 6.43 g of 2-(4-nitrophenoxy)ethanol. The obtained solid was taken for the next step without further purification.

Workup

  1. customInto a 100 mL 3-neck RBF equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureAfter completion, the reaction mixture was cooled to room temperature
  4. filtrationSolid precipitate was filtered
  5. washwashed with water
  6. customSolid material was dried under reduced pressure at 45° C. for 1 hr

Sources & evidence

ORD record
ord-af0865af77784b4a9bf07572bbe2d54a
Source dataset
uspto-grants-2016_08
Patent number
US09415049B2

Reaction notes

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