2,6-Dimethoxyphenol → 1,2,3-Trimethoxybenzene

HRID 1358701Notes

Reaction equation

HRID 1358701 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[OH:11].N12CCCN=C1CCCC[CH2:13]2>CCOC(C)=O.O>[CH3:10][O:9][C:5]1[C:4]([O:11][CH3:13])=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 70412,6-DimethoxyphenolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 124621,2,3-Trimethoxybenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2,6-dimethoxyphenol (1.0 g, 6.49 mmol) in DMC (10 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)(0.99 g, 6.49 mmol) was added and the resulting solution was heated to reflux (90° C.) for 4.5 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 H2O (40 mL), 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 trimethoxybenzene as a solid. The yield of trimethoxybenzene as deteremined by HPLC was 99%.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureThe reaction was cooled to ambient temperature
  3. customThe organic layer was separated
  4. washwashed in sequence with H2O (40 mL), 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-1ed21fe6644443e78dbac737b078de78
Source dataset
uspto-grants-2003_07
Patent number
US06596877B2

Reaction notes

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