Acetic Anhydride → 2-Acetoxymethyl-6-chloropyridine

HRID 1975744Notes

Reaction equation

HRID 1975744 reaction equation
[Cl:1][C:2]1[N+:7]([O-])=[C:6]([CH3:9])[CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[C:15]([O:18]C(=O)C)(=[O:17])[CH3:16]>C(OCC)(=O)C>[C:15]([O:18][CH2:9][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 45797722-Chloro-6-methylpyridine 1-oxide

Product 1

HCID 107261902-Acetoxymethyl-6-chloropyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the 6-chloro-2-methylpyridine-N-oxide prepared in step 1 in 750 mL acetic anhydride was heated at reflux overnight. The reaction was cooled to ambient temperature and poured into saturated aqueous sodium bicarbonate. The mixture was diluted with ethyl acetate and filtered through celite. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and concentrated. The residue was azeotroped with benzene to remove any remaining acetic acid. 2-acetoxymethyl-6-chloropyridine was isolated by vacuum distillation (b.p. 105°-110° C./1.3 torr).

Workup

  1. temperatureat reflux overnight
  2. filtrationfiltered through celite
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was azeotroped with benzene
  8. customto remove any remaining acetic acid

Sources & evidence

ORD record
ord-0e8521110d084798887e9448661bfaab
Source dataset
uspto-grants-1994_02
Patent number
US05288743

Reaction notes

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