Sulfuric Acid → Ethyl 4-(4-oxocyclohexyl)benzoate

HRID 2237389Notes

Reaction equation

HRID 2237389 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]4[O:18][CH2:19][C:20](C)(C)N=4)=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1.S(=O)(=O)(O)[OH:25]>C(O)C>[O:4]=[C:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:18][CH2:19][CH3:20])=[O:25])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 598366992-[4-(1,4-Dioxaspiro[4,5]dec-8-yl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole

Product 1

HCID 22633634Ethyl 4-(4-oxocyclohexyl)benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3 g of the product of step (iii) (9.51 mmol) are dissolved in 60 ml of ethanol and 4.0 ml of 96% sulphuric acid are added, and the mixture is refluxed for 22 hours. The solvent is partially evaporated off and the remaining mixture is taken up with a mixture of 300 ml of a saturated sodium bicarbonate solution and 150 ml of ethyl acetate. The organic phase is washed with a saturated aqueous NaCl solution. The organic phase is dried and, after filtration, the solvent is evaporated off under reduced pressure. The crude product is purified by chromatography on a silica gel column, eluting with an 8/2 hexane-ethyl acetate mixture. The compound of the title is obtained in the form of a solid.

Workup

  1. temperaturethe mixture is refluxed for 22 hours
  2. customThe solvent is partially evaporated off
  3. additionthe remaining mixture is taken up with a mixture of 300 ml of a saturated sodium bicarbonate solution and 150 ml of ethyl acetate
  4. washThe organic phase is washed with a saturated aqueous NaCl solution
  5. customThe organic phase is dried
  6. filtrationafter filtration
  7. customthe solvent is evaporated off under reduced pressure
  8. customThe crude product is purified by chromatography on a silica gel column
  9. washeluting with an 8/2 hexane-ethyl acetate mixture
  10. customThe compound of the title is obtained in the form of a solid

Sources & evidence

ORD record
ord-d6933e9362254e1f866d7d6b8cd455bf
Source dataset
uspto-grants-2010_05
Patent number
US07718646B2

Reaction notes

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