3-(4-methoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole → 2-methyl-4-(1-methyl-1H-pyrazol-3-yl)-phenol

HRID 628505Notes

Reaction equation

HRID 628505 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[CH:12][N:11]([CH3:14])[N:10]=2)=[CH:5][C:4]=1[CH3:15]>C(O)(=O)C>[CH3:15][C:4]1[CH:5]=[C:6]([C:9]2[CH:13]=[CH:12][N:11]([CH3:14])[N:10]=2)[CH:7]=[CH:8][C:3]=1[OH:2]

Participants

3

Reactant 1

HCID 1182362533-(4-methoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole

Product 1

HCID 1367563942-methyl-4-(1-methyl-1H-pyrazol-3-yl)-phenolYield 90.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-(4-methoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole 2.9 g, 47% hydrobromic acid 21 ml and acetic acid 21 ml was stirred with heating under reflux for twenty hours. The solvent was distilled off and to the resulting residues was added ethyl acetate 100 ml, and the resulting mixture was stirred at room temperature for one hour. The precipitates were filtered and were washed with hexane, and were concentrated under reduced pressure to give 2-methyl-4-(1-methyl-1H-pyrazol-3-yl)-phenol 2.45 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for twenty hours
  3. distillationThe solvent was distilled off and to the resulting residues
  4. additionwas added ethyl acetate 100 ml
  5. stirringthe resulting mixture was stirred at room temperature for one hour
  6. filtrationThe precipitates were filtered
  7. washwere washed with hexane
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-5f0ca30cd6794285852c9cbde3b852cd
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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