Hydrochloric Acid → 4-Methoxymethyl-1-naphthoic acid

HRID 1610214Notes

Reaction equation

HRID 1610214 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]([O:16]C)=[O:15])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>CO>[CH3:1][O:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]([OH:16])=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22262055Methyl 4-((methyloxy)methyl)-1-naphthalenecarboxylate

Product 1

HCID 127491544-Methoxymethyl-1-naphthoic acidYield 84.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-((methyloxy)methyl)-1-naphthalenecarboxylate (780 mg, 3.38 mmol) in methanol (10 ml) was added 1N aqueous sodium hydroxide solution (6.76 ml, 6.76 mmol), and the mixture was stirred overnight at room temperature. 1N Hydrochloric acid was added to the reaction solution (10 ml) and the mixture was extracted with ethyl acetate (50 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give 4-((methyloxy)methyl)-1-naphthalenecarboxylic acid (615 mg, 84%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 ml×2)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b506196bb33044dc95dd6b32d2ab9121
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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