Sulfuric Acid → 3-Oxaspiro[5.5]undec-7-en-9-one

HRID 2116627Notes

Reaction equation

HRID 2116627 reaction equation
S(=O)(=O)(O)O.[O:6]1[CH2:11][CH2:10][CH:9]([CH:12]=O)[CH2:8][CH2:7]1.[CH:14]([C:16]([CH3:18])=[O:17])=[CH2:15]>C1C=CC=CC=1>[CH2:10]1[C:9]2([CH2:12][CH2:18][C:16](=[O:17])[CH:14]=[CH:15]2)[CH2:8][CH2:7][O:6][CH2:11]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6570Methyl vinyl ketone2×HCID 9964078Tetrahydro-2H-pyran-4-carboxaldehyde

Product 1

HCID 687636893-Oxaspiro[5.5]undec-7-en-9-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.5 ml of sulphuric acid is added to 317 mmol of tetrahydro-2H-pyran-4-carboxaldehyde and 317 mmol of methyl vinyl ketone in 500 ml of benzene. The reaction mixture is then refluxed for 3 hours, water being removed using a Dean-Stark apparatus, and then a further 317 mmol of methyl vinyl ketone are added and reflux is continued for 3 hours. The mixture is subsequently washed, dried and then concentrated, and the residue obtained is distilled to yield the expected product.

Workup

  1. temperatureThe reaction mixture is then refluxed for 3 hours
  2. customwater being removed
  3. temperaturereflux
  4. washThe mixture is subsequently washed
  5. customdried
  6. concentrationconcentrated
  7. customthe residue obtained
  8. distillationis distilled

Sources & evidence

ORD record
ord-cf09498ba1c74e9e8c858088b4efb334
Source dataset
uspto-grants-2008_10
Patent number
US07439263B2

Reaction notes

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