Hydrochloric Acid → Methyl 4-(4-oxocyclohexyl)benzoate

HRID 1443421Notes

Reaction equation

HRID 1443421 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1.Cl>C1COCC1>[O:4]=[C:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=2)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59881361Methyl 4-(1,4-dioxaspiro[4.5]dec-8-yl)benzoate

Product 1

HCID 15023908Methyl 4-(4-oxocyclohexyl)benzoateYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(1,4-dioxaspiro[4.5]dec-8-yl)benzoate (480 mg, 1.73 mmol) in 8 mL of THF was added 4 mL of 1 N of aqueous HCl solution. The mixture was stirred at rt for 21 h and concentrated. The residue was partitioned between 50 mL of Et2O and 50 mL of 1 N aqueous NaHCO3 solution. The organic layer was separated, dried over MgSO4, and concentrated. Chromatography on a Biotage 40S cartridge using 1:9 v/v EtOAc/hexanes as the eluant afforded 343 mg (85%) of the title compound.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between 50 mL of Et2O and 50 mL of 1 N aqueous NaHCO3 solution
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4531bd434b754a839dd4498cacac1dea
Source dataset
uspto-grants-2010_02
Patent number
US07659294B2

Reaction notes

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