alpha-(2,3-Dichloro-4-methoxyphenyl)-2-pyridinemethanol → (2,3-Dichloro-4-methoxyphenyl)(2-pyridyl)methanone

HRID 568642Notes

Reaction equation

HRID 568642 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[OH:12]>C(O)(=O)C.O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[O:12]

Participants

4

Reactant 1

HCID 13015690alpha-(2,3-Dichloro-4-methoxyphenyl)-2-pyridinemethanol

Product 1

HCID 13015691(2,3-Dichloro-4-methoxyphenyl)(2-pyridyl)methanone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

α-(2,3-dichloro-4-methoxyphenyl)-2-pyridinemethanol (31.86 g) is dissolved in 600 ml of acetic acid and 100 ml of H2O. Chromic anhydride (11.0 g) is added portionwise over five minutes. After three hours the reaction mixture is poured into H2O and extracted with ether. The combined organic phase is washed well with 10% NaHCO3, then brine, and dried. Removal of the solvent under reduced pressure gives a crystalline product of (2,3-dichloro-4-methoxyphenyl)(2-pyridyl)methanone, mp 104°-107° C.

Workup

  1. extractionextracted with ether
  2. washThe combined organic phase is washed well with 10% NaHCO3
  3. dry with materialbrine, and dried
  4. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-8c050c8c35dc4a1e9a7d8c8ca8fcd5f6
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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