Water → 4-(Benzyloxy)-2-methylaniline

HRID 388016Notes

Reaction equation

HRID 388016 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 saline 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 saline
  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-f35f0068f8aa4c618e625440f4af3184
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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