Methyl 4-(hydroxymethyl)naphthalene-1-carboxylate → 1-Naphthalenecarboxylic acid, 4-formyl-, methyl ester

HRID 1610210Notes

Reaction equation

HRID 1610210 reaction equation
[OH:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:5][CH:4]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:5][CH:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 10878557Methyl 4-(hydroxymethyl)naphthalene-1-carboxylate

Product 1

HCID 103308541-Naphthalenecarboxylic acid, 4-formyl-, methyl esterYield 85%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of methyl 4-(hydroxymethyl)-1-naphthalenecarboxylate (2.0 g, 9.25 mmol) in chloroform (40 ml) was added manganese dioxide (4.0 g), and the mixture was stirred at room temperature for 2 hrs. Manganese dioxide was filtered from the reaction solution using celite and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) and recrystallized from ethyl acetate-hexane to give methyl 4-formyl-1-naphthalenecarboxylate (1.41 g, 85%).

Workup

  1. filtrationManganese dioxide was filtered from the reaction solution
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)
  4. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-591087b8658046d6bb8bd2350134b508
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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