4-Hydroxybenzaldehyde → 4-(Benzo[d]oxazol-2-yl)phenol

HRID 338813Notes

Reaction equation

HRID 338813 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].[OH:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.C(OCC)(=O)C>C(O)(=O)C.O>[O:13]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:19]1[C:18]1[CH:21]=[CH:22][C:15]([OH:14])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 58012-AminophenolHCID 8857Ethyl AcetateHCID 517045Sodium Acetate

Product 1

HCID 27855874-(Benzo[d]oxazol-2-yl)phenolYield 7.6%

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-hydroxybenzaldehyde (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 ethyl acetate (4:1) to obtain a solid Compound 123.

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-f5b5a6df9896469d8af277a477b18517
Source dataset
uspto-grants-2014_11
Patent number
US08889881B2

Reaction notes

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