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

HRID 652874Notes

Reaction equation

HRID 652874 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-1bb34bc2005e44fa9dab3b6ebdd2a1ac
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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