Acetic Acid → Spiro[5.5]undec-1-en-3-one

HRID 500093Notes

Reaction equation

HRID 500093 reaction equation
[CH3:1][C:2]([CH:4]=[CH2:5])=[O:3].C([O-])(=O)C.[Na+].C(O)(=O)C.O.[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)(=O)C>[CH:5]1[C:16]2([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:22][CH2:1][C:2](=[O:3])[CH:4]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 1140TolueneHCID 6570Methyl vinyl ketoneHCID 517045Sodium Acetate

Product 1

HCID 323824Spiro[5.5]undec-1-en-3-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the above product (1) (22.6 g) in toluene (100 ml) was added methylvinyl ketone (9.6 g), and the mixture was stirred at room temperature. After 3 hours, to the reaction mixture were added sodium acetate (10 g), acetic acid (40 ml) and water (40 ml), and the mixture was heated under reflux. After 4 hours, the reaction mixture was cooled to room temperature and then ethyl acetate (100 ml) was added thereto. The mixture was washed with water (100 ml), 2 mol/l hydrochloric acid (50 ml) and then brine (100 ml), and the organic layer was dried over sodium sulfate, and the solvent was removed in vacuo. The residue was distilled under reduced pressure (95° C., 1 mmHg) to give 4.3 g of spiro[5.5]undecen-3-one.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. waitAfter 4 hours
  4. temperaturethe reaction mixture was cooled to room temperature
  5. washThe mixture was washed with water (100 ml), 2 mol/l hydrochloric acid (50 ml)
  6. dry with materialbrine (100 ml), and the organic layer was dried over sodium sulfate
  7. customthe solvent was removed in vacuo
  8. distillationThe residue was distilled under reduced pressure (95° C., 1 mmHg)

Sources & evidence

ORD record
ord-a6fbb871a94547ca80457568a791ba3c
Source dataset
uspto-grants-2010_08
Patent number
US07767854B2

Reaction notes

Loading…