alpha-(1-Methylpyrazol-5-yl)-2,3-dichloro-4,5-dimethoxybenzylalcohol → (1-Methylpyrazol-5-yl)-(2,3-dichloro-4,5-dimethoxyphenyl)-methanone

HRID 1074185

Reaction equation

HRID 1074185 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]([OH:20])[C:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([Cl:18])[C:9]=2[Cl:19])=[CH:5][CH:4]=[N:3]1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][N:2]1[C:6]([C:7]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([Cl:18])[C:9]=2[Cl:19])=[O:20])=[CH:5][CH:4]=[N:3]1

Participants

4

Reactant 1

HCID 14748635alpha-(1-Methylpyrazol-5-yl)-2,3-dichloro-4,5-dimethoxybenzylalcohol

Product 1

HCID 14748594(1-Methylpyrazol-5-yl)-(2,3-dichloro-4,5-dimethoxyphenyl)-methanoneYield 90.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

20 g of manganese dioxide are added to a solution of 7.08 g of α-(1-methylpyrazol-5-yl)-2,3-dichloro-4,5-dimethoxybenzylalcohol in methylene chloride and the mixture is stirred at room temperature for 3 days. The reaction mixture is filtered and washed with chloroform. The filtrate and the washings are combined and evaporated to remove solvent. The residue is crystallized from n-hexane to give 6.35 g of (1-methylpyrazol-5-yl)-(2,3-dichloro-4,5-dimethoxyphenyl)-methanone.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washwashed with chloroform
  3. customevaporated
  4. customto remove solvent
  5. customThe residue is crystallized from n-hexane

Sources & evidence

ORD record
ord-181450a5f63b4b1a94992e22718c4cc2
Source dataset
uspto-grants-1990_11
Patent number
US04973600

Linked notes

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