Water → 4-(Benzyloxy)-2-methylaniline

HRID 1010403Notes

Reaction equation

HRID 1010403 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([OH:8])=[CH:6][CH:7]=1.[H-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>CS(C)=O.CCCCCC.C(OCC)(=O)C.C(OCC)C.O1CCCC1>[CH2:12]([O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([CH3:9])[CH:4]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 178194-Amino-m-cresolHCID 24758Sodium hydride

Product 1

HCID 167730534-(Benzyloxy)-2-methylanilineYield 75.7%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 21226206Ethyl acetate hexaneSolventHCID 21868444Ether tetrahydrofuranSolvent

Procedure

After dissolving 4-amino-3-cresol (10 g, 81.20 mmol) in dimethylsulfoxide (80 ml), sodium hydride (3.25 g, 81.20 mmol, 60% in oil) was added and the mixture was stirred for 15 minutes at room temperature under a nitrogen atmosphere. Benzyl bromide (4.83 ml, 40.60 mmol) was added, and the mixture was stirred overnight at room temperature under a nitrogen atmosphere. Water was added to the reaction solution, extraction was performed with diethyl ether/tetrahydrofuran, the extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was adsorbed onto silica gel, purified by silica gel column chromatography (hexane-ethyl acetate-ethanol) and then by NH silica gel column chromatography (hexane-ethyl acetate) to obtain the title compound (6.55 g, 30.72 mmol, 75.64%) as a violet oil.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred overnight at room temperature under a nitrogen atmosphere
  3. washthe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. custompurified by silica gel column chromatography (hexane-ethyl acetate-ethanol)

Sources & evidence

ORD record
ord-0757248998684ad896700dda3beb7dd2
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

Loading…