Formaldehyde → 3,4-Dihydro-6-methoxy-2-methylene-1(2h)-naphthalenone

HRID 432594Notes

Reaction equation

HRID 432594 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.C=O.F[C:17](F)(F)C([O-])=O.C[NH2+]C1C=CC=CC=1.CCOCC>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[C:8](=[CH2:17])[CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 3283Diethyl EtherHCID 141126-Methoxy-alpha-tetraloneHCID 2724109N-Methylanilinium trifluoroacetate

Product 1

HCID 113444693,4-Dihydro-6-methoxy-2-methylene-1(2h)-naphthalenone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-methoxytetralone (29.24 g, 165.9 mmol), paraformaldehyde (22.4 g, 746.6 mmol) and N-methylanilinium trifluoroactate (55 g, 248.9 mmol) in 250 mL THF was refluxed for 4 hours and allowed to come to room temperature. To this was added ether (250 mL) with stirring and the mixture was decanted to remove the gummy precipitate. The supernatant was washed with sat. NaHCO3, the oganic layer was dried (MgSO4) and concentrated. The residue was redissolved in ether, filtered through celite and concentrated to afford the title compound as a thick yellow oil.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customto come to room temperature
  3. customthe mixture was decanted
  4. customto remove the gummy precipitate
  5. washThe supernatant was washed with sat. NaHCO3
  6. dry with materialthe oganic layer was dried (MgSO4)
  7. concentrationconcentrated
  8. dissolutionThe residue was redissolved in ether
  9. filtrationfiltered through celite
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c7eb14bfbdd84499bd6a79efe0b6eb5b
Source dataset
uspto-grants-2003_12
Patent number
US06664250B2

Reaction notes

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