Hydrochloric Acid → Ethyl 2-(4-oxocyclohexyl)acetate

HRID 1404408Notes

Reaction equation

HRID 1404408 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7][CH2:6]2)[O:4]CC1.Cl.C([O-])(O)=O.[Na+]>C(#N)C>[O:4]=[C:5]1[CH2:10][CH2:9][CH:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 15700391Ethyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetate

Product 1

HCID 12666966Ethyl 2-(4-oxocyclohexyl)acetateYield 82.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetate (from Step 1, Example 77, 4.71 g, 19.44 mmol) in acetonitrile (45 mL) was added 6N HCl aqueous solution (45 mL). The resulting mixtures was stirred at rt for 2 h and neutralized with solid NaHCO3 to pH 8, extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4. Filtration and evaporation to dryness gave the ketone product as colorless oil (2.97 g, 78.1%).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration and evaporation to dryness

Sources & evidence

ORD record
ord-c228ad51bba74dabb7470fc68aeacb88
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

Loading…