Acetic Acid → (4-Chlorophenyl) 2-pyridyl ketone

HRID 2399041Notes

Reaction equation

HRID 2399041 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[Cl:12][C:13]1[CH:25]=[CH:24][C:16]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:15][CH:14]=1.C(O)(=[O:28])C>O>[Cl:12][C:13]1[CH:25]=[CH:24][C:16]([C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[O:28])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 25408Sodium DichromateHCID 780542-(4'-Chlorobenzyl)pyridine

Product 1

HCID 80594(4-Chlorophenyl) 2-pyridyl ketone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

164 G. (0.55 mol) of sodium dichromate was added to a stirred solution of 101 g. (0.5 mol) of 2-(p-chlorobenzyl)-pyridine in 450 ml. of acetic acid and the resulting mixture was stirred and refluxed for 3 hrs. The resulting dark green solution was cooled and poured into 1500 ml. of cold water. The precipitate which resulted was collected, washed with water and air dried to yield 2-(4-chlorobenzoyl)pyridine as white microprisms, mp. 62°-64° C. (ligroin).

Workup

  1. temperaturerefluxed for 3 hrs
  2. temperatureThe resulting dark green solution was cooled
  3. additionpoured into 1500 ml
  4. customThe precipitate which resulted
  5. customwas collected
  6. washwashed with water and air
  7. customdried

Sources & evidence

ORD record
ord-8e942d6359e94ffc95b6f170da0cd870
Source dataset
uspto-grants-1977_05
Patent number
US04026936

Reaction notes

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