Acetic Acid → HCID 118271388, compound

HRID 628517Notes

Reaction equation

HRID 628517 reaction equation
COC1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([CH3:14])=[C:12]([CH3:15])[N:11]([CH3:16])[N:10]=2)=[CH:5][C:4]=1C.Br.[C:19]([OH:22])(=O)[CH3:20]>>[CH3:16][N:11]1[C:12]([CH3:15])=[C:13]([CH3:14])[C:9]([C:6]2[C:7]([CH3:8])=[C:19]([OH:22])[CH:20]=[CH:4][CH:5]=2)=[N:10]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 118001326HCID 118001326, compound

Product 1

HCID 118271388HCID 118271388, compound

Procedure

A mixture of 3-(4-methoxy-3-methyl-phenyl)-1,4,5-trimethyl-1H-pyrazole (described in Reference Preparation example 65) 0.6 g, 47% hydrobromic acid 5 ml and acetic acid 5 ml was stirred with heating under reflux for thirteen hours. The solvent was distilled off and to the resulting residues was added ethyl acetate 30 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 (1,4,5-trimethyl-1H-pyrazol-3-yl)-2-methyl-phenol 0.5 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for thirteen hours
  3. distillationThe solvent was distilled off and to the resulting residues
  4. additionwas added ethyl acetate 30 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-bceb47853def45b8ac1f5f1d6f1fdc34
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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