Methyl iodide → 7-Methoxy-2-naphthol

HRID 1772268Notes

Reaction equation

HRID 1772268 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:12].[C:13]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[CH3:13][O:12][C:2]1[CH:1]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([OH:11])=[CH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 113972,7-NaphthalenediolHCID 11430Potassium Carbonate

Product 1

HCID 8531737-Methoxy-2-naphtholYield 37%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of naphthalene-2,7-diol (25 g, 156.08 mmol) and K2CO3 (32.3 g, 232.02 mmol) in acetone (300 ml) was added iodomethane (22.2 g, 156.41 mmol) dropwise with stirring at 0° C. The resulting solution was stirred overnight at room temperature. The solids were filtered off and the filtrate was concentrated under vacuum to give a residue, which was purified by silica gel column chromatography using 1%-10% ethyl acetate in petroleum ether to afford 7-methoxynaphthalen-2-ol as a light yellow solid (10 g, 37%). (ES, m/z): [M+H]+ 175.1; 1H NMR (400 MHz, DMSO-d6): δ 9.65 (s, 1H), 7.65 (d, J=8.8 Hz, 2H), 6.79 (dd, J=13.6, 1.6 Hz, 2H), 6.92-6.89 (m, 2H), 3.84 (s, 3H).

Workup

  1. stirringThe resulting solution was stirred overnight at room temperature
  2. filtrationThe solids were filtered off
  3. concentrationthe filtrate was concentrated under vacuum
  4. customto give a residue, which
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-64075ac6f05445f49181d5d6611fcf6b
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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