Benzyl Chloride → 5-(Benzyloxy)-1,3-dimethyl-2-nitrobenzene

HRID 1284956Notes

Reaction equation

HRID 1284956 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[C:6]([CH3:11])[C:7]=1[N+:8]([O-:10])=[O:9].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:13]([O:12][C:4]1[CH:5]=[C:6]([CH3:11])[C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[CH:3]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 1384663,5-Dimethyl-4-nitrophenol

Product 1

HCID 133699565-(Benzyloxy)-1,3-dimethyl-2-nitrobenzeneYield 84.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3,5-dimethyl-4-nitrophenol (17.6 g), benzyl chloride (20.0 g) and anhydrous K2CO3 (13.2 g) in acetone (100 ml) is stirred under reflux for 22 hours. The reaction mixture is filtered and the precipitate washed with acetone. The acetone extract is concentrated in vacuo and the residue short path distilled (160°-170° C; 50μ) to give 22.9 grams of an orange liquid which crystallized on standing.

Workup

  1. temperatureunder reflux for 22 hours
  2. filtrationThe reaction mixture is filtered
  3. washthe precipitate washed with acetone
  4. extractionThe acetone extract
  5. concentrationis concentrated in vacuo
  6. distillationthe residue short path distilled (160°-170° C; 50μ)

Sources & evidence

ORD record
ord-58eaf6a8556e4072946148ff9dc712e0
Source dataset
uspto-grants-1986_01
Patent number
US04564640

Reaction notes

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