m-Chloroperbenzoic acid → HCID 57073118, compound

HRID 1977291Notes

Reaction equation

HRID 1977291 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[CH:15]=[CH:14][C:13](C=O)=[CH:12][CH:11]=2)[CH:9]=1)=[O:4].ClC1C=CC=C(C(OO)=[O:26])C=1>ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:26])=[CH:12][CH:11]=2)[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 57286669HCID 57286669, compound

Product 1

HCID 57073118HCID 57073118, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(4-formylphenyl)-1H-pyrazol-4-carboxylic acid methyl ester (5.0 g) in dichloromethane (100 ml) was treated with 3-chloroperbenzoic acid for 5 minutes at room temperature. The solution was heated at 50° C. for 4 hours, during which period additional 3-chloroperbenzoic acid (1.87 g) was added. After concentration, methanol (150 ml) and potassium carbonate (9.00 g) were added to the residue, and the mixture was stirred for 14 hours at ambient temperature. The reaction mixture was poured into water, adjusted to pH 8 with 1N HCl and the resulting precipitate was collected by filtration to give 1-(4-hydroxyphenyl)-1H-pyrazol-4-carboxylic acid methyl ester (0.51 g).

Workup

  1. additionwas added
  2. concentrationAfter concentration, methanol (150 ml) and potassium carbonate (9.00 g)
  3. additionwere added to the residue
  4. additionThe reaction mixture was poured into water
  5. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-d854c991b95b4446be52dba69f7d4c2d
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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