Water → Methyl 4-nitrobenzyl ether

HRID 1057267Notes

Reaction equation

HRID 1057267 reaction equation
[H-].[Na+].I[CH3:4].O.[N+:6]([C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1)([O-:8])=[O:7]>O1CCCC1>[CH3:4][O:14][CH2:13][C:12]1[CH:11]=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 692754-Nitrobenzyl alcohol

Product 1

HCID 316176Methyl 4-nitrobenzyl etherYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

16 g (60%) of sodium hydride was dispersed in 20 ml of tetrahydrofuran. To this, 100 ml of a solution in which 50 g of p-nitrobenzyl alcohol was dissolved in tetrahydrofuran, was added in drops while cooling with ice. The mixture was stirred for one hour at room temperature, and thereafter 56 g of iodomethane was added in drops while cooling with ice, and the mixture was further stirred for 3 hours at room temperature. To the reaction solution was added water, and a mixture was extracted with ethyl acetate. The extracted solvent was distilled off under reduced pressure, and the resulting product was purified by silica gel chromatography to obtain 40 g of p-methoxymethylnitrobenzene.

Workup

  1. additionwas added in drops
  2. temperaturewhile cooling with ice
  3. temperaturewhile cooling with ice
  4. stirringthe mixture was further stirred for 3 hours at room temperature
  5. extractiona mixture was extracted with ethyl acetate
  6. distillationThe extracted solvent was distilled off under reduced pressure
  7. customthe resulting product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0e37fd49e768424aabe7fc7407a8e128
Source dataset
uspto-grants-2003_02
Patent number
US06514656B1

Reaction notes

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