[3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazol-4-yl]methanol → 3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazole-4-carbaldehyde

HRID 2221698Notes

Reaction equation

HRID 2221698 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:9]([CH2:10][OH:11])=[CH:8][N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[N:6]=1>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:9]([CH:10]=[O:11])=[CH:8][N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[N:6]=1

Participants

4

Reactant 1

HCID 69217086[3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazol-4-yl]methanol

Product 1

HCID 230763813-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazole-4-carbaldehydeYield 81%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 1140TolueneSolvent

Procedure

A mixture of [3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazol-4-yl]methanol (2.39 g), activated manganese dioxide (5.0 g) and toluene (30 mL) was stirred at room temperature for 8 hrs. Activated manganese dioxide (5.0 g) was added and the mixture was further stirred for 12 hrs. Manganese dioxide was removed by filtration, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:9-1:2, v/v) to give 3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazole-4-carbaldehyde as an orange oil (1.65 g, yield 81%).

Workup

  1. stirringthe mixture was further stirred for 12 hrs
  2. customManganese dioxide was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. washeluted with ethyl acetate-hexane (1:9-1:2

Sources & evidence

ORD record
ord-fec724e4b59a46e49fcadbe36e140ee0
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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