Dimethyl Sulfate → HCID 10036901, compound

HRID 355472Notes

Reaction equation

HRID 355472 reaction equation
[OH:1][C:2]1[C:3]([C:14]([OH:16])=[O:15])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2.[C:17](=O)([O-])O.[Na+].S(OC)(OC)(=O)=O>CN(C)C=O>[OH:1][C:2]1[C:3]([C:14]([O:16][CH3:17])=[O:15])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 6083303-Hydroxy-7-methoxy-2-naphthoic acid

Product 1

HCID 10036901HCID 10036901, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

6.55 g of 3-hydroxy-7-methoxy-naphthalene-2-carboxylic acid were dissolved in 20 ml of dimethylformamide, treated with 5.5 g of sodium hydrogen carbonate and 4.0 ml of dimethyl sulfate and stirred at 90° C. under argon for 10 minutes. Subsequently, the reaction mixture was poured on to ice-water and extracted with ether. The combined ether phases were washed with water, dried over magnesium sulfate and concentrated. The thus-obtained residue was recrystallized from ethyl acetate/hexane. Methyl 3-hydroxy-7-methoxy-naphthalene-2-carboxylate with m.p. 138° C. was thus obtained.

Workup

  1. extractionextracted with ether
  2. washThe combined ether phases were washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe thus-obtained residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d0f244c4b44e44619ff11f138c7e8378
Source dataset
uspto-grants-1998_11
Patent number
US05830920

Reaction notes

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