Hydrochloric Acid → 6-Methoxy-2-naphthol

HRID 1857096Notes

Reaction equation

HRID 1857096 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=2)[CH:9]=1.S(OC)(OC)(=O)=O.Cl>CN(C)C=O>[CH3:1][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([OH:18])[CH:12]=[CH:11]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 935522,6-Dihydroxynaphthalene

Product 1

HCID 2886346-Methoxy-2-naphtholYield 29.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (1.244 g) was added to a solution of commercially available 2,6-dihydroxynaphthalene (961 mg) in N,N-dimethylformamide (100 ml), and the admixture was stirred at room temperature for 30 minutes. Dimethyl sulfate (1.14 ml) was slowly added dropwise to the mixture and the resulting mixture was further stirred at room temperature overnight. The reaction mixture thus prepared was neutralized with a 2N HCl solution and then partitioned between water and ethyl acetate, and the ethyl acetate layer was dried with anhydrous magnesium sulfate. After removing the solvent by distillation under reduced pressure, the resulting residue was purified by column chromatography on silica gel (eluting with chloroform/ethyl acetate) to obtain 307 mg of the title compound (yield: 29%).

Workup

  1. stirringthe resulting mixture was further stirred at room temperature overnight
  2. customThe reaction mixture thus prepared
  3. custompartitioned between water and ethyl acetate
  4. dry with materialthe ethyl acetate layer was dried with anhydrous magnesium sulfate
  5. customAfter removing the solvent
  6. distillationby distillation under reduced pressure
  7. customthe resulting residue was purified by column chromatography on silica gel (eluting with chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-80aefd137f3c469fbc11448879578fb8
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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