Water → 1,2-dimethoxynaphthalene

HRID 2185895Notes

Reaction equation

HRID 2185895 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1O.[H-].[Na+].COS([O:20][CH3:21])(=O)=O.O.[CH3:23]N(C=O)C>CCOCC>[CH3:23][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:20][CH3:21]

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 113181,2-DihydroxynaphthaleneHCID 24758Sodium hydride

Product 1

HCID 2992571,2-dimethoxynaphthaleneYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the solution of 1,2-dihydroxynaphthalene (5 g, 31.2 mmol) in DMF (140 mL) was added NaH (3.0 g, 75.0 mmol). After stirred at room temperature for 1 h, dimethylsulfate (7.09 mL, 75.0 mmol) was added. After stirring at room temperature for 22 h, water and Et2O was added, the organic layer was washed with brine, water, dried (MgSO4), filtered and concentrated. Column chromatography yielded the title compound as a colorless oil (3.83 g, 65%). 1H NMR (CDCl3) δ 8.12 (d, 1H), 7.79 (d, 1H), 7.59 (d, 1H), 7.47 (m, 1H), 7.35 (m, 1H), 7.29 (d, 1H), 3.99 (s, 3H), 3.99 (s, 3H).

Workup

  1. stirringAfter stirring at room temperature for 22 h
  2. washthe organic layer was washed with brine, water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9af0f5c5033040b08f4ef0def446bdbb
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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