8-Benzylidene-1,4-dioxaspiro[4.5]decane → 4-Benzylidenecyclohexanone

HRID 530507Notes

Reaction equation

HRID 530507 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>CC(C)=O.Cl.O>[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 1

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

Product 1

HCID 197051964-BenzylidenecyclohexanoneYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19044839Acetone hydrogen chlorideSolvent

Procedure

Under vigorous stirring, at rt, 8-benzylidene-1,4-dioxaspiro-[4.5]-decane (1.8 g, 7.81 mmol) was dissolved in a acetone/HCl (10% v/v) mixture (70 mL:35 mL) and left to stir 4 h. The crude mixture was diluted in water and extracted with AcOEt (3×40 mL). The combined organic fractions were washed with brine, dried over Na2SO4, filtered and concentrated to dryness to afford pure title compound (1.4 g, 96%) as colorless oil. 1H NMR (CDCl3): δ 2.44 (t, J=7.0 Hz, 2H), 2.53 (t, J=6.8 Hz, 2H), 2.65-2.72 (m, 2H), 2.74-2.80 (m, 2H), 6.49 (s, 1H), 7.21-7.27 (m, 3H), 7.32-7.39 (m, 2H).

Workup

  1. waitleft
  2. extractionextracted with AcOEt (3×40 mL)
  3. washThe combined organic fractions were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-79f0f2864d17428b8d038b6f4163e7b6
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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