Pyridine → 4-(Benzoyloxy)cyclohexanone

HRID 1719090Notes

Reaction equation

HRID 1719090 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(Cl)(=O)[C:13]1[CH:18]=[CH:17]C=[CH:15][CH:14]=1.N1C=CC=CC=1.[O:27]1CCCC1>C(OCC)(=O)C>[C:3]([O:4][CH:5]1[CH2:6][CH2:7][C:8](=[O:11])[CH2:9][CH2:10]1)(=[O:27])[C:2]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Product 1

HCID 2426774-(Benzoyloxy)cyclohexanoneYield 43%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1,4-dioxaspiro[4.5]decan-8-ol (4.44 g), benzoyl chloride (3.9 mL), pyridine (2.7 mL) and tetrahydrofuran (50 mL) was stirred at room temperature for 12 hr. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was dissolved in tetrahydrofuran (50 mL), and 6 M hydrochloric acid (4.7 mL) was added thereto, and then the mixture was stirred at 60° C. for 12 hr. The reaction mixture was diluted with ethyl acetate, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate, and the combined organic layer was successively washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound as a pale yellow oil (2.64 g, 43%).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in tetrahydrofuran (50 mL)
  5. addition6 M hydrochloric acid (4.7 mL) was added
  6. stirringthe mixture was stirred at 60° C. for 12 hr
  7. additionThe reaction mixture was diluted with ethyl acetate
  8. customthe organic layer was separated
  9. extractionThe aqueous layer was extracted with ethyl acetate
  10. washthe combined organic layer was successively washed with water and saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1203987d9bf54416bcc25f0cdf7c489a
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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