Methyl iodide → 3-Methoxy-2-naphthoic acid

HRID 1981818Notes

Reaction equation

HRID 1981818 reaction equation
[OH:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[H-].[Na+].[CH3:17]I>CN(C)C=O>[CH3:17][O:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 71043-Hydroxy-2-naphthoic acidHCID 24758Sodium hydride

Product 1

HCID 701613-Methoxy-2-naphthoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Five grams of 2-hydroxy-3-naphthoic acid was dissolved in 220 ml of dimethyl formamide, 3.74 grams of sodium hydride was added thereto little by little with ice cooling and stirring, then 11.0 grams of methyl iodide was added, and the mixture was stirred at room temperature for twelve hours. The reaction solution was partitioned between benzene and water, the benzene layer was collected, dried over anhydrous magnesium sulfate, the solvent was evaporated therefrom, and the residue was dried. To this were added 10 ml of water, 90 ml of methyl cellosolve and 5.0 grams of potassium hydroxide, the mixture was heated to reflux for forty minutes with stirring, the reaction solution was poured over ice water, the mixture was acidified with diluted hydrochloric acid, and the separated mass was extracted with ethyl acetate. The ethyl acetate extract was dried over anhydrous magnesium sulfate, the solvent was evaporated therefrom, and the residue was crystallized from n-hexane to afford 2-methoxy-3-naphthoic acid. The yield was 4.62 grams.

Workup

  1. stirringthe mixture was stirred at room temperature for twelve hours
  2. customThe reaction solution was partitioned between benzene and water
  3. customthe benzene layer was collected
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customthe residue was dried
  7. additionTo this were added 10 ml of water, 90 ml of methyl cellosolve and 5.0 grams of potassium hydroxide
  8. temperaturethe mixture was heated
  9. temperatureto reflux for forty minutes
  10. stirringwith stirring
  11. additionthe reaction solution was poured over ice water
  12. extractionthe separated mass was extracted with ethyl acetate
  13. extractionThe ethyl acetate extract
  14. dry with materialwas dried over anhydrous magnesium sulfate
  15. customthe solvent was evaporated
  16. customthe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-4fa52efa1d1547fdac4876046ac74083
Source dataset
uspto-grants-1986_06
Patent number
US04593025

Reaction notes

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