4-Nitrophenol → 1-{2-[2-(2-Methoxyethoxy)ethoxy]ethoxy}-4-nitrobenzene

HRID 78705

Reaction equation

HRID 78705 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].[N+:28]([C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1)([O-:30])=[O:29]>CN(C=O)C.O>[CH3:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:37][C:34]1[CH:35]=[CH:36][C:31]([N+:28]([O-:30])=[O:29])=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 99488982-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

Product 1

HCID 146918221-{2-[2-(2-Methoxyethoxy)ethoxy]ethoxy}-4-nitrobenzeneYield 94.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 16 (1.83 g, 5.75 mmol) in anhydrous DMF (10 mL) were added K2CO3 (2.39 g, 17.3 mmol) and 4-nitrophenol (0.78 g, 5.59 mmol), and the reaction mixture was heated to 80° C. for 16 h. After cooling, the mixture was diluted in water, extracted three times with DCM, and then dried over MgSO4. The filtrate was concentrated under reduced pressure to give an oily residue, which was purified by flash chromatography over silica gel with Hex/EtOAc (1:2) to afford 17 as a yellow oil (1.51 g, 92%): 1H NMR (500 MHz, CDCl3) δ 8.19 (d, J=9.1 Hz, 2H), 6.97 (d, J=9.1 Hz, 2H), 4.26-3.65 (m, 12H), 3.37 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. extractionextracted three times with DCM
  3. dry with materialdried over MgSO4
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give an oily residue, which
  6. customwas purified by flash chromatography over silica gel with Hex/EtOAc (1:2)

Sources & evidence

ORD record
ord-2394a121b57540eea619009698c28bfe
Source dataset
uspto-grants-2014_09
Patent number
US08841460B2

Linked notes

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