Water → 2-(Benzyloxy)-4-methyl-1-nitrobenzene

HRID 1032517Notes

Reaction equation

HRID 1032517 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 127886-Nitro-m-cresol

Product 1

HCID 136293042-(Benzyloxy)-4-methyl-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

61.2 g of 3-hydroxy-4-nitrotoluene, 66.3 g of potassium carbonate, and 54.7 ml of benzyl chloride are heated in 800 ml of dimethylformamide to 100° C. for 1.5 hours; after cooling, the mixture is poured into water, and the thus-precipitated material is recrystallized from ethanol, yielding 82.0 g of 3-benzyloxy-4-nitrotoluene, mp 49°-51° C.

Workup

  1. temperatureafter cooling
  2. customthe thus-precipitated material is recrystallized from ethanol

Sources & evidence

ORD record
ord-e8d9e7cfa91741b4b83133dbbdc0a416
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

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