Sulfuric Acid → 4-Benzylidenecyclohexanone

HRID 2406241Notes

Reaction equation

HRID 2406241 reaction equation
[CH:1](=[C:8]1[CH2:17][CH2:16][C:11]2(OCC[O:12]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O>C1COCC1>[CH:1](=[C:8]1[CH2:17][CH2:16][C:11](=[O:12])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 154177378-Benzylidene-1,4-dioxaspiro[4.5]decane

Product 1

HCID 197051964-BenzylidenecyclohexanoneYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-benzylidene-1,4-dioxaspiro[4.5]decane (5.79 g, 25.1 mmol) in THF (126 mL) a solution of H2SO4 (10% in water, 67 mL) was added and the result mixture was stirred at room temperature for 3 days. THF was removed under reduce pressure and water was added. The aqueous phase was extracted with DCM and the organic layers were combined, washed with brine, dried with Na2SO4, filtered and concentrated to give 4-Benzylidenecyclohexanone (4.35 g 84%) as a yellowish oil: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.23-7.33 (m, 2 H), 7.13-7.20 (m, 3 H), 6.42 (s, 1 H), 2.67-2.77 (m, 2 H), 2.62 (t, J=7.0 Hz, 2 H), 2.46 (t, J=7.0 Hz, 2 H), 2.37 (t, J=7.0 Hz, 2 H).

Workup

  1. customTHF was removed
  2. additionwas added
  3. extractionThe aqueous phase was extracted with DCM
  4. washwashed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8f9f37d23bb349daab760a39bf06d23f
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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