Hydrochloric Acid → 2-Methoxy-1-naphthoic acid

HRID 1604223Notes

Reaction equation

HRID 1604223 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[C:15]([O:17]C)=[O:16].COC1C=CC2C(=CC=CC=2)C=1C([O-])=O.[Na+].Cl>CO.O>[CH3:3][O:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[C:15]([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 604022Methyl 2-methoxy-1-naphthoate2×HCID 23686469HCID 23686469, compound

Product 1

HCID 703562-Methoxy-1-naphthoic acidYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

50% Aqueous sodium hydroxide was added to a solution of this methyl 2-methoxynaphthoate in methanol (400 mL). The mixture was refluxed, and water (300 mL) was added at a rate which kept the forming sodium 2-methoxynaphthoate in solution. After the water was added, the reaction was refluxed an additional 3 hours, then allowed to stand at room temperature overnight. The resulting solid mass was acidified with concentrated HCl, then was diluted with water (1 liter) and the product collected by filtration. Vacuum drying gave 50.96 g of 2-methoxy-1-naphthoic acid, a 95% yield.

Workup

  1. temperatureThe mixture was refluxed
  2. temperaturethe reaction was refluxed an additional 3 hours
  3. filtrationthe product collected by filtration
  4. customVacuum drying

Sources & evidence

ORD record
ord-4941fc8fbab8470c8cdb12a30d001148
Source dataset
uspto-grants-1999_11
Patent number
US05994270

Reaction notes

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