Acetic Acid → 2-(4-Oxocyclohexyl)pyridine N-oxide

HRID 1383779Notes

Reaction equation

HRID 1383779 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N+:12]=3[O-:17])[CH2:7][CH2:6]2)[O:4]CC1.C(O)(=O)C.Cl.[OH-].[Na+]>O>[O:4]=[C:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N+:12]=2[O-:17])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 206685242-(1,4-Dioxaspiro[4.5]dec-8-yl)pyridine N-oxide

Product 1

HCID 206685372-(4-Oxocyclohexyl)pyridine N-oxideYield 73.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

2-(1,4-Dioxaspiro[4.5]dec-8-yl)pyridine N-oxide (3 g, 12.75 mmol) was combined with glacial acetic acid (20 mL), concentrated hydrochloric acid (10 mL), and water (10 mL). The resulting mixture was heated to 45° C. for 24 hours. The reaction was cooled to 0° C. and the pH was adjusted to 6 with 20% sodium hydroxide solution. The phases were separated and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with water and brine, then dried (sodium sulfate), and concentrated under reduced pressure to yield 1.8 g of the product as an oil.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customThe phases were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-56b8392d8d41402aa69e5dff9da9555e
Source dataset
uspto-grants-2001_07
Patent number
US06255315B1

Reaction notes

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