1-Naphthol → 1-Methoxynaphthalene

HRID 1358703Notes

Reaction equation

HRID 1358703 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:12]1CCN2C(=NCCC2)CC1>CCOC(C)=O.O>[CH3:12][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 70051-NaphtholHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 166681-Methoxynaphthalene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-naphthol (1.0 g, 6.94 mmol) in DMC (10 mL), DBU (1.06 g, 6.94 mmol) was added and the resulting mixture was heated to reflux (90° C.) for 16 hours. The reaction was cooled to ambient temperature and diluted with EtOAc (50 mL) and H2O (40 mL). The organic layer was separated and washed in sequence with 2M HCl (2×40 mL), 2M NaOH (2×40 mL) and H2O. The organic layer was dried over Na2SO4, filtered and concentrated under vacuum to give 1-methoxynaphthalene as an oil. The yield of 1-methoxynaphthalene as determined by HPLC was 99% conversion.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureThe reaction was cooled to ambient temperature
  3. customThe organic layer was separated
  4. washwashed in sequence with 2M HCl (2×40 mL), 2M NaOH (2×40 mL) and H2O
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2a0ae7fb9eb8401eaf673f8391cbadbe
Source dataset
uspto-grants-2003_07
Patent number
US06596877B2

Reaction notes

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