N,N-Dimethylaniline → 6-Methoxy-1-(2-propenyl)-2-naphthol

HRID 460447Notes

Reaction equation

HRID 460447 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([O:13][CH2:14]C=C)[CH:7]=[CH:6]2.CN(C)[C:19]1[CH:24]=CC=C[CH:20]=1>>[CH3:14][O:13][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4]([CH2:24][CH:19]=[CH2:20])=[C:3]([OH:2])[CH:12]=[CH:11]2

Participants

3

Reactant 2

HCID 949N,N-DimethylanilineHCID 22718066HCID 22718066, compound

Product 1

HCID 227180506-Methoxy-1-(2-propenyl)-2-naphtholYield 82%

Procedure

6-Methoxy-2-(2-propenyloxy)naphthalene (24.9 g, 116.2 mmol) was dissolved in N,N-dimethyl aniline (100 ml) followed by heating under reflux for 15 hours. After the organic solvent was distilled off under reduced pressure, 2N aqueous hydrochloric acid was added to the residue, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/4), followed by recrystallization from ethyl acetate/hexane, to give 6-methoxy-1-(2-propenyl)-2-naphthol (20.3 g, Yield 82%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 15 hours
  3. distillationAfter the organic solvent was distilled off under reduced pressure, 2N aqueous hydrochloric acid
  4. additionwas added to the residue, which
  5. extractionwas then extracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationAfter distilling off the solvent
  9. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/4)
  10. customfollowed by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b5a9916f0ec540149d3f9c2e2f43e634
Source dataset
uspto-grants-2007_03
Patent number
US07196081B2

Reaction notes

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