Hydrogen Bromide → Methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenol

HRID 628504Notes

Reaction equation

HRID 628504 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH3:14])=[C:12]([CH3:15])[C:11]([CH3:16])=[N:10]2)=[CH:5][C:4]=1[CH3:17].Br>C(O)(=O)C>[CH3:17][C:4]1[CH:5]=[C:6]([N:9]2[C:13]([CH3:14])=[C:12]([CH3:15])[C:11]([CH3:16])=[N:10]2)[CH:7]=[CH:8][C:3]=1[OH:2]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 1182365881-(4-Methoxy-3-methylphenyl)-3,4,5-trimethyl-1H-pyrazole

Product 1

HCID 118236550Methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenolYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(4-methoxy-3-methyl-phenyl)-3,4,5-trimethyl-1H-pyrazole (described in Reference Preparation example 33) 7.3 g, 47% hydrobromic acid 50 ml and acetic acid 50 ml was stirred with heating under reflux for thirty hours. The solvent was distilled off and to the resulting residues was added ethyl acetate 400 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-(3,4,5-trimethyl-pyrazol-1-yl)-phenol 6.1 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for thirty hours
  3. distillationThe solvent was distilled off and to the resulting residues
  4. additionwas added ethyl acetate 400 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-0b4585798953484aa49f526ff94ddc14
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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