HCID 117724701, compound → HCID 136941920, compound

HRID 628541Notes

Reaction equation

HRID 628541 reaction equation
[CH3:1][N:2]1[C:6]([O:7][CH3:8])=[C:5]([CH3:9])[C:4]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C(C)C)=[C:12]([CH3:20])[CH:11]=2)=[N:3]1>S(=O)(=O)(O)O>[CH3:1][N:2]1[C:6]([O:7][CH3:8])=[C:5]([CH3:9])[C:4]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([CH3:20])[CH:11]=2)=[N:3]1

Participants

3

Reactant 1

HCID 117724701HCID 117724701, compound

Product 1

HCID 136941920HCID 136941920, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1,4-dimethyl-3-(4-isopropoxy-3-methyl-phenyl)-5-methoxy-1H-pyrazole (described in Reference Preparation example 98) 7.4 g and 306 aqueous sulfuric acid solution 100 ml was stirred with heating under reflux for fifteen hours. Next, the following work-up treatments was carried out. The reaction mixture was cooled to 0° C., and the resulting precipitates were filtered and were washed with cool water to give some solids. Again, the filtrate were concentrated under reduced pressure to about a half volume and were cooled to 0° C., and the resulting precipitates were filtered and were washed with cool water to give some solids. These work-up treatments were carried out four times and the resulting all solids were dried under reduced pressure to give 4-(1,4-dimethyl-5-methoxy-1H-pyrazol-3-yl)-2-methyl-phenol 6.4 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for fifteen hours
  3. customthe resulting precipitates
  4. filtrationwere filtered
  5. washwere washed with cool water
  6. customto give some solids
  7. concentrationAgain, the filtrate were concentrated under reduced pressure to about a half volume
  8. temperaturewere cooled to 0° C.
  9. customthe resulting precipitates
  10. filtrationwere filtered
  11. washwere washed with cool water
  12. customto give some solids
  13. customthe resulting all solids were dried under reduced pressure

Sources & evidence

ORD record
ord-00416d87cc3b4db790a765bead1f0bca
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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