Sulfuric Acid → HCID 136941918, compound

HRID 628548Notes

Reaction equation

HRID 628548 reaction equation
[Cl:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C(C)C)=[C:12]([CH3:20])[CH:11]=2)=[N:4][N:5]([CH3:9])[C:6]=1[O:7][CH3:8].S(=O)(=O)(O)O>>[Cl:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([CH3:20])[CH:11]=2)=[N:4][N:5]([CH3:9])[C:6]=1[O:7][CH3:8]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 117724773HCID 117724773, compound

Product 1

HCID 136941918HCID 136941918, compoundYield 25%

Procedure

A mixture of 4-chloro-3-(4-isopropoxy-3-methyl-phenyl)-5-methoxy-1-methyl-1H-pyrazole (described in Reference Preparation example 111) 5.6 g and 30% aqueous sulfuric acid solution 60 ml was stirred with heating under reflux for 20 hours. Thereto was added ice water 10 ml and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, and was dried over anhydrous magnesium sulfate and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 4-(4-Chloro-5-methoxy-1-methyl-1H-pyrazol-3-yl)-2-methyl-phenol 1.2 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 20 hours
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-e378fdb6050047bda1f1c6012a257f6c
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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