Ammonium → 3-Methyl-4-(1,3-oxazol-4-yl)phenol

HRID 396794

Reaction equation

HRID 396794 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[CH3:12])=O.[NH4+:13].[OH-].[Na+].[CH:16]([OH:18])=O>>[CH3:12][C:6]1[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=1[C:3]1[N:13]=[CH:16][O:18][CH:2]=1

Participants

5

Reactant 4

HCID 223AmmoniumHCID 284Formic AcidHCID 14798Sodium HydroxideHCID 178121702-Bromo-1-(4-hydroxy-2-methylphenyl)ethanone

Product 1

HCID 223167433-Methyl-4-(1,3-oxazol-4-yl)phenolYield 13%

Procedure

A mixture of 2-bromo-1-(4-hydroxy-2-methylphenyl)-1-ethanone (18 g, 78 mmol), ammonium fornate (17 g, 273 mmol) in formic acid (100 ml) was heated at reflux temperature for 3 hours. The mixture was cooled down to room temperature and made basic by addition of 50% NaOH aqueous solution at 0° C. The whole was extracted with CH2Cl2. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:5) to give title compound (1.8 g, 13% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 3 hours
  3. extractionThe whole was extracted with CH2Cl2
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate-hexane (1:5)

Sources & evidence

ORD record
ord-fc7e71fb491f444197c07957526684df
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Linked notes

Loading…