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

HRID 1074187Notes

Reaction equation

HRID 1074187 reaction equation
[Cl:1][O-].[Na+].[CH3:4][N:5]1[C:9]([CH:10]([OH:23])[C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([Cl:21])[C:12]=2[Cl:22])=[CH:8][CH:7]=[N:6]1>C(O)(=O)C>[CH3:4][N:5]1[C:9]([C:10]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([Cl:21])[C:12]=2[Cl:22])=[O:23])=[C:8]([Cl:1])[CH:7]=[N:6]1

Participants

4

Reactant 2

HCID 14748635alpha-(1-Methylpyrazol-5-yl)-2,3-dichloro-4,5-dimethoxybenzylalcoholHCID 23665760Sodium Hypochlorite

Product 1

HCID 14748633(1-Methyl-4-chloropyrazol-5-yl)-(2,3-dichloro-4,5-dimethoxyphenyl)-methanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

19.3 g of an aqueous 10% sodium hypochlorite solution are added to a solution of 3.9 g of α-(1-methylpyrazol-5-yl)-2,3-dichloro-4,5-dimethoxybenzylalcohol in acetic acid and the mixture is stirred at room temperature for 2 hours. The reaction mixture is concentrated to remove acetic acid, and ethyl acetate is added to the residue. The organic layer is separated, washed with water, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography to give 2.1 g of (1-methyl-4-chloropyrazol-5-yl)-(2,3-dichloro-4,5-dimethoxyphenyl)-methanone.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customto remove acetic acid, and ethyl acetate
  3. additionis added to the residue
  4. customThe organic layer is separated
  5. washwashed with water
  6. customdried
  7. customevaporated
  8. customto remove solvent
  9. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-39634b30ff004d2190ff7dc883dbc121
Source dataset
uspto-grants-1990_11
Patent number
US04973600

Reaction notes

Loading…