Methanol → 1,4-Naphthalenedimethanol

HRID 1166729Notes

Reaction equation

HRID 1166729 reaction equation
[C:1]1([C:14](O)=[O:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](O)=[O:12])=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO>C1COCC1>[OH:12][CH2:11][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]([CH2:14][OH:15])=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 690651,4-Naphthalenedicarboxylic acidHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 155367531,4-NaphthalenedimethanolYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 1,4-Naphthalenedicarboxylic acid (25 g, 116 mmol) was dripped into a mixture of Lithium Aluminum Hydride (15 g, 395 mmol) in 600 mL of anhydrous THF and refluxed for two days. The mixture was cooled in an ice bath and excess LAH was decomposed by the slow addition of methanol followed by ice chips. THF was removed under vacuum and the residue was acidified with 1N HCl. The product was extracted with ethyl acetate (3×), washed with aqueous sodium bicarbonate (3×), water, brine, and dried over magnesium sulfate. 1,4-Bishydroxymethylnaphthalene (70%) was obtained as a solid after evaporation of the solvent and can be used in the subsequent oxidation step without further purification. A portion of the material was purified by column chromatography using hexane/ethyl acetate (80/20 to 75/25) for characterization purposes.

Workup

  1. temperaturerefluxed for two days
  2. temperatureThe mixture was cooled in an ice bath
  3. customTHF was removed under vacuum
  4. extractionThe product was extracted with ethyl acetate (3×)
  5. washwashed with aqueous sodium bicarbonate (3×), water, brine
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-b1c5f5313ada493ab2fd0636977e6acf
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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