Hydrochloric Acid → 4-(Benzo[D][1,3]dioxol-5-YL)cyclohex-3-enone

HRID 1893217Notes

Reaction equation

HRID 1893217 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3(O)[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.Cl>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 151996894-Benzo[1,3]dioxol-5-yl-4-hydroxycyclohexanone

Product 1

HCID 595419144-(Benzo[D][1,3]dioxol-5-YL)cyclohex-3-enone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-benzo[1,3]dioxol-5-yl-4-hydroxy-cyclohexanone (as prepared in the previous step, 3.5 g, 15 mmol) in THF (10 mL) was treated with 6N HCl (5 mL) overnight under argon at room temperature. The resulting solution was quenched with sufficient 1N NaOH to neutralize the reaction. The solvent was removed and the residue was partitioned between DCM and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give a yellow oil, which was then purified by silica gel column on a CombiFlash® system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as a white solid.

Workup

  1. customThe resulting solution was quenched with sufficient 1N NaOH
  2. customthe reaction
  3. customThe solvent was removed
  4. customthe residue was partitioned between DCM and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a yellow oil, which
  10. customwas then purified by silica gel column on a CombiFlash® system

Sources & evidence

ORD record
ord-f3f6f92178074950b773e80510465149
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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