Hydrochloric Acid → Ethyl 1-methyl-4-oxocyclohexanecarboxylate

HRID 1913235Notes

Reaction equation

HRID 1913235 reaction equation
[CH3:1][C:2]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:11][CH2:10][C:5]2(OCC[O:6]2)[CH2:4][CH2:3]1.CCO.O.Cl>O1CCOCC1>[CH3:1][C:2]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:3][CH2:4][C:5](=[O:6])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 19004805Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate

Product 1

HCID 21911973Ethyl 1-methyl-4-oxocyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a 50 mL round-bottom flask was mixed with ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate (Int-6a, 1.99 g, 8.72 mmol), EtOH (10 mL), H2O (5 mL), and 4N HCl in 1,4-dioxane (5 mL). The resulting solution was stirred at room temperature for 64 hours. At this time, the solvent was removed in vacuo and the residue was taken up in DCM. The suspension was washed with saturated NaHCO3(aq) and the organic layer was dried over Na2SO4. The resulting product was taken on without further purification. Yield=1.00 g.

Workup

  1. customAt this time, the solvent was removed in vacuo
  2. washThe suspension was washed with saturated NaHCO3(aq)
  3. dry with materialthe organic layer was dried over Na2SO4
  4. customThe resulting product was taken on without further purification

Sources & evidence

ORD record
ord-d027fab779754691829fdfd85cf0c6a8
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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