Methyl iodide → 5-Methoxynaphthalen-1-ol

HRID 1470485Notes

Reaction equation

HRID 1470485 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:13][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[C:7]2[OH:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 67491,5-DihydroxynaphthaleneHCID 11430Potassium Carbonate

Product 1

HCID 110629015-Methoxynaphthalen-1-olYield 44.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1,5-dihydroxy naphthalene (40 g, 0.25 mol) in dry acetone (200 mL) was added, K2CO3 (34.5 g, 0.25 mol) and the mixture was stirred at RT for 3 h, and then cooled to 0° C. To this, a solution of methyl iodide (124.5 mL, 2 mol) in dry acetone (100 mL) was added drop wise and the reaction mixture was stirred for 2 h at 0° C. and then for 10 h at RT. After completion (TLC), the mixture was filtered and washed with EtOAc. The solvent was removed under reduced pressure and the crude product was purified by column chromatography (8% EtOAc:Hexanes) to afford the desired compound (19.2 g, 44%) as a light green solid.

Workup

  1. waitfor 10 h at RT
  2. filtrationAfter completion (TLC), the mixture was filtered
  3. washwashed with EtOAc
  4. customThe solvent was removed under reduced pressure
  5. customthe crude product was purified by column chromatography (8% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-5101b83e05344f9da3eab90306fefd3c
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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