2-(4-Methoxy-phenyl)-4,5-dimethyl-oxazole → 4-(4,5-Dimethyl-2-oxazolyl)phenol

HRID 2165417Notes

Reaction equation

HRID 2165417 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)=[CH:5][CH:4]=1>Br>[CH3:14][C:12]1[N:13]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)[O:10][C:11]=1[CH3:15]

Participants

3

Reactant 1

HCID 189829612-(4-Methoxy-phenyl)-4,5-dimethyl-oxazole

Product 1

HCID 1356214744-(4,5-Dimethyl-2-oxazolyl)phenolYield 81.6%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 32.0 g of 2-(4-methoxyphenyl)-4,5-dimethyloxazole and 250 ml of 48% hydrogen bromide solution was stirred and heated at reflux for 2.5 hours. The reaction mixture was concentrated in vacuo, the residue dissolved in 2N sodium hydroxide and the solution acidified with acetic acid. The solid product was collected and recrystallized from methanol to give 24.3 g of 4-(4,5-dimethyl-2-oxazolyl)phenol, m.p. 202°-203° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2.5 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue dissolved in 2N sodium hydroxide
  5. customThe solid product was collected
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-47f18b4145954df98fa21fd47fc7e040
Source dataset
uspto-grants-1990_07
Patent number
US04939267

Reaction notes

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