Methanol → 1-(Methoxymethyl)-3-nitrobenzene

HRID 1274368Notes

Reaction equation

HRID 1274368 reaction equation
[H-].[Na+].[CH3:3][OH:4].C(OC1C=CC(O[C:18]2[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][C:19]=2[N+:26]([O-:28])=[O:27])=CC=1)C1C=CC=CC=1>O>[CH3:3][O:4][CH2:22][C:21]1[CH:24]=[CH:25][CH:18]=[C:19]([N+:26]([O-:28])=[O:27])[CH:20]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 22120979HCID 22120979, compound

Product 1

HCID 113896091-(Methoxymethyl)-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60% Oily sodium hydride (0.22 g, 5.5 mmol) was added to methanol (50 ml) under ice-cooling, and after stirring at room temperature for 30 minutes, 4-[4-(benzyloxy)phenoxy]-3-nitrobenzyl chloride (1.00 g, 2.7 mmol) was added thereto, followed by stirring for 3 hours. The reaction solution was poured into water and extracted with ethyl acetate. After drying, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography [eluent; hexane - chloroform (1:1)] to give 1-[4-benzyloxy)phenoxy]-4-(methoxymethyl)-2-nitrobenzene (0.92 g).

Workup

  1. temperaturecooling
  2. stirringby stirring for 3 hours
  3. extractionextracted with ethyl acetate
  4. customAfter drying
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [eluent; hexane - chloroform (1:1)]

Sources & evidence

ORD record
ord-ce256404ffb34f99a13738da8b2b9ab7
Source dataset
uspto-grants-2000_12
Patent number
US06156801

Reaction notes

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