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

HRID 1166738Notes

Reaction equation

HRID 1166738 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>ClCCl.O=[Mn]=O>[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 ester

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-hydroxymethylnaphthoate above (3.3, 15.3 mmol) in dichloromethane (20 mL) was added MnO2 (6.6 g, 76 mmol). After stirring the dark mixture for 16 hours, the insolubles were filtered through a bed of Celite. Evaporation of the solvent gave the desired product as a white solid in quantitative yield.

Workup

  1. filtrationthe insolubles were filtered through a bed of Celite
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5c1e4bce41b8420a91628cc80a02b3b1
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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