Ethyl orthoformate → 6-Methylbenzoxazole

HRID 1685072Notes

Reaction equation

HRID 1685072 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[CH:6][C:7]=1[OH:8].[CH:10](OCC)(OCC)OCC>C1(C)C=CC=CC=1>[CH3:9][C:5]1[CH:4]=[CH:3][C:2]2[N:1]=[CH:10][O:8][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 760822-Amino-5-methylphenol

Product 1

HCID 27249696-MethylbenzoxazoleYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 50 ml flask was charged with 6-amino-m-cresol (2 g, 16.24 mmole), 20 ml toluene and 5.4 ml triethyl orthoformate. The reaction mixture was refluxed for 2 hours. The mixture was concentrated down to about 2.3 g crude. Purification by silicagel column chromatography using 20% EtOAc/hexane provided 1.45 g brown oil (69% yield) that solidified in the freezer.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. concentrationThe mixture was concentrated down to about 2.3 g crude
  3. customPurification by silicagel column chromatography

Sources & evidence

ORD record
ord-76b5d78008954aaab6599abdc088afca
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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