2-Amino-4-methylphenol → 5-Methylbenzoxazole

HRID 911331Notes

Reaction equation

HRID 911331 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Cl-].[CH3:11]N(C=NC=[N+](C)C)C>O1CCOCC1>[CH3:8][C:6]1[CH:5]=[CH:4][C:3]2[O:9][CH:11]=[N:1][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 72642-Amino-4-methylphenolHCID 11008255Gold's Reagent

Product 1

HCID 27249705-MethylbenzoxazoleYield 65%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Combine 2-amino-4-methyl-phenol (1.0 g, 8.12 mmol), [(dimethylaminomethylene-aminomethylene)dimethylammonium chloride (Gold's reagent) (1.6 g, 9.91 mmol), anhydrous 1,4-dioxane (25 mL) and reflux for 17 h. Cool the reaction mixture to ambient temperature, evaporate the solvent and purify by chromatography on silica gel eluting with hexane/EtOAc (9:1) to obtain the desired intermediate as a yellow oil (0.7 g, 65%).

Workup

  1. customevaporate the solvent
  2. custompurify by chromatography on silica gel eluting with hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-e87c18367d3846af8ba61ef330318e1b
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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