3-Nitrophenol → 1-[(4-Methoxyphenyl)Methoxy]-3-nitro-Benzene

HRID 2175375Notes

Reaction equation

HRID 2175375 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1>CN(C)C=O>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][O:12][C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 111373-NitrophenolHCID 14798Sodium HydroxideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 36283881-[(4-Methoxyphenyl)Methoxy]-3-nitro-BenzeneYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaOH (0.54 g, 13.36 mmol) was added into 10 ml of degassed dimethylformamide at 0° C., then 3-nitrophenol (1.69 g, 12.14 mmol) dissolved in 7 ml of dimethylformamide was dropped slowly, and then para-methoxybenzylchloride (1.81 ml, 13.36 mmol) was added slowly. After stirred for 2 hours at the increased reaction temperature to room temperature, the reaction mixture was extracted using saturated ammonium chloride (100 ml) and ethylacetate (100 ml). The organic layer was washed twice using 100 ml of water, and dried using anhydrous sodium sulfate, then concentrated under vacuum. The resultant solid was solidified using n-hexane to obtain pale yellowish solid of 1-(4-methoxybenzyloxy)-3-nitrobenzene (2.85 g, 90%) finally.

Workup

  1. additionwas dropped slowly
  2. extractionthe reaction mixture was extracted
  3. washThe organic layer was washed twice
  4. customdried
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-779889f54f344b84b4183475117ea034
Source dataset
uspto-grants-2015_06
Patent number
US09062066B2

Reaction notes

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