Hydrochloric Acid → Cyclohexanone, 4-(4-pyridinyl)-

HRID 1193342Notes

Reaction equation

HRID 1193342 reaction equation
Cl.O1[C:6]2([CH2:11][CH2:10][CH:9]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[CH2:8][CH2:7]2)[O:5]CC1>C1COCC1>[N:15]1[CH:16]=[CH:17][C:12]([CH:9]2[CH2:8][CH2:7][C:6](=[O:5])[CH2:11][CH2:10]2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 578925724-(4-Pyridyl)cyclohexanone ethylene ketal

Product 1

HCID 10154273Cyclohexanone, 4-(4-pyridinyl)-Yield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 M HCl (13.6 ml) was added to a solution of 4-(1,4-dioxaspiro[4.5]decan-8-yl)pyridine (3.0 g, 13.6 mmol, 1 eq) in THF (136 ml), and stirring was carried out for 3 h at RT. The solvent was removed under reduced pressure. The residue was diluted with water (50 ml) and rendered basic with solid sodium hydrogen carbonate. Then extraction with ethyl acetate (2×100 ml) was carried out. The combined organic phases were washed with water (80 ml), dried over sodium sulfate and concentrated under reduced pressure. The desired product was used in the next step without being purified further. Yield: 69% (1.65 g, 9.42 mmol).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with water (50 ml)
  3. extractionThen extraction with ethyl acetate (2×100 ml)
  4. washThe combined organic phases were washed with water (80 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customwithout being purified further

Sources & evidence

ORD record
ord-173c05bd90a345788de64512bf96573f
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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