Methyl iodide → 2,4-Dimethylspiro[5.5]undeca-1,4,8-trien-3-one

HRID 1633411Notes

Reaction equation

HRID 1633411 reaction equation
CN([CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([OH:12])=[C:7]([CH3:13])[CH:6]=1)C.CI.[CH2:16]=[CH:17][CH:18]=[CH2:19]>C(OCC)(=O)C>[CH3:13][C:7]1[C:8](=[O:12])[C:9]([CH3:11])=[CH:10][C:5]2([CH2:19][CH2:18][CH:17]=[CH:16][CH2:4]2)[CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 78451,3-ButadieneHCID 39355Phenol, 4-[(dimethylamino)methyl]-2,6-dimethyl-

Product 1

HCID 135314552,4-Dimethylspiro[5.5]undeca-1,4,8-trien-3-oneYield 87.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a 250 mL glass reaction vessel containing an ethyl acetate (120 mLs) solution of N,N-dimethyl,2,6-dimethyl-4-aminomethylphenol (3.58 g; 20 mmols), there was added methyl iodide (20 mmols) to give a colorless slurry. The reaction vessel was sealed and 1,3-butadiene (100 mmols) was introduced into the system. The reaction mixture was heated to 120° C. and the pressure was increased from atmospheric up to 70 psig. The reaction mixture was maintained at these conditions for approximately 16 hours. The reaction vessel was then cooled to room temperature. After cooling, the reaction mixture was filtered to remove ammonium iodide salt by-product. The filtrate was concentrated to afford a viscous oil which was crystallized from ethanol to give 3.3 g of 2,4-dimethylspiro[5.5]undeca-1,4,8-trien-3-one (84% yield by vapor phase chromatography).

Workup

  1. customto give a colorless slurry
  2. customThe reaction vessel was sealed
  3. temperaturethe pressure was increased from atmospheric up to 70 psig
  4. temperatureThe reaction mixture was maintained at these conditions for approximately 16 hours
  5. temperatureThe reaction vessel was then cooled to room temperature
  6. temperatureAfter cooling
  7. filtrationthe reaction mixture was filtered
  8. customto remove ammonium iodide salt by-product
  9. concentrationThe filtrate was concentrated
  10. customto afford a viscous oil which
  11. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-0a1ddec862814f128d3b64edba878b33
Source dataset
uspto-grants-1984_10
Patent number
US04480133

Reaction notes

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