2-Aminophenol → 2-(4-methoxyphenyl)-1,3-benzoxazole

HRID 338814Notes

Reaction equation

HRID 338814 reaction equation
C([O-])(=O)C.[Na+].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.C(OCC)(=O)C>C(O)(=O)C.O>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]2[O:13][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[N:6]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 58012-AminophenolHCID 8857Ethyl AcetateHCID 312444-MethoxybenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 4838372-(4-methoxyphenyl)-1,3-benzoxazoleYield 6.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In an acetic acid solvent in the presence of sodium acetate (NaOAc) (3.0 eq.), a solution including 2-aminophenol (1.0 eq.) and 4-methoxybenzaldehyde (1.0 eq.) was refluxed. After cooling, the reaction mixture was distributed between ethyl acetate and water, and an organic layer was dried, filtered, and evaporated. The residual was purified by silica gel column chromatography using hexane and acetone (25:1) to obtain a solid Compound 124.

Workup

  1. temperaturewas refluxed
  2. temperatureAfter cooling
  3. customan organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residual was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d015f08ebf204b40b0e85693c78973ad
Source dataset
uspto-grants-2014_11
Patent number
US08889881B2

Reaction notes

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