Hydrochloric Acid → Methyl 4-(hydroxymethyl)naphthalene-1-carboxylate

HRID 1610209Notes

Reaction equation

HRID 1610209 reaction equation
C([O:4][CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][CH:7]=1)(=O)C.[OH-].[Na+].Cl>CO>[OH:4][CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22261906Methyl 4-((acetyloxy)methyl)-1-naphthalenecarboxylate

Product 1

HCID 10878557Methyl 4-(hydroxymethyl)naphthalene-1-carboxylateYield 85.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-((acetyloxy)methyl)-1-naphthalenecarboxylate (3.91 g, 15.1 mmol) in methanol (20 ml) was added 1N aqueous sodium hydroxide solution (15.1 ml, 15.1 mmol), and the mixture was stirred at room temperature for 5 min. 1N Hydrochloric acid was added to the reaction solution (20 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 purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give methyl 4-(hydroxymethyl)-1-naphthalenecarboxylate (2.78 g, 85%).

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 purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-d80340142ccc401ba1e1087fa16ad116
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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