Ethylene Glycol → 2-(4-Nitrophenoxy)ethanol

HRID 2274251Notes

Reaction equation

HRID 2274251 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

In a 50 mL, 3-neck RBF equipped with a magnetic stirrer, reflux condenser, and thermo pocket were sequentially charged 4-fluoro nitrobenzene (2.00 g), Cs2CO3 (9.21 g) and ethylene glycol (20 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 of the reaction, the reaction mixture was cooled to room temperature and poured into cold water. Solid precipitate was filtered and washed with water. Solid was dried under reduced pressure at 45° C. for 1 hr. 2.70 g of 2-(4-nitrophenoxy)ethanol was obtained as a solid and was taken for the next step without further purification.

Workup

  1. customIn a 50 mL, 3-neck RBF equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was cooled to room temperature
  5. filtrationSolid precipitate was filtered
  6. washwashed with water
  7. customSolid was dried under reduced pressure at 45° C. for 1 hr

Sources & evidence

ORD record
ord-5ec084fcb53c4a7387c8fa5c1a7d3b8c
Source dataset
uspto-grants-2015_09
Patent number
US09126950B2

Reaction notes

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