Hydrochloric Acid → 1-[4-(Trifluoromethyl)pyridin-2-yl]ethanone

HRID 1755986Notes

Reaction equation

HRID 1755986 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][N:7]=1)=[CH2:5])C.Cl>CC(C)=O>[C:4]([C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:13])[F:14])[CH:9]=[CH:8][N:7]=1)(=[O:3])[CH3:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19392517HCID 19392517, compound

Product 1

HCID 103301301-[4-(Trifluoromethyl)pyridin-2-yl]ethanoneYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1-ethoxy-1-(4-trifluoromethylpyrid-2-yl)-ethylene (1.4 g) in acetone (15 ml) was treated with hydrochloric acid (5 ml of a 2M solution). The reaction mixture was allowed to stand for 16 hours then concentrated, diluted with water and neutralised with sodium bicarbonate. The aqueous phase was extracted with ether (×2) and the combined extracts were washed with brine, dried and concentrated to give 2-acetyl-4-trifluoromethylpyridine (1.2 g, 99% yield) as a pale yellow liquid. IR maximum (film): 1705 cm-1.

Workup

  1. concentrationthen concentrated
  2. additiondiluted with water and neutralised with sodium bicarbonate
  3. extractionThe aqueous phase was extracted with ether (×2)
  4. washthe combined extracts were washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6bf2f42bb10d43d8b1526a23aa8fec15
Source dataset
uspto-grants-1995_08
Patent number
US05439910

Reaction notes

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