1,4-Naphthalenedicarboxylic acid → 1,4-Naphthalenedimethanol

HRID 2379030Notes

Reaction equation

HRID 2379030 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:20](O)=[O:21])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17](O)=[O:18])=[CH:9][CH:8]=1>C1COCC1>[C:10]1([CH2:17][OH:18])[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([CH2:20][OH:21])=[CH:8][CH:9]=1

Participants

4

Reactant 2

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

Product 1

HCID 155367531,4-NaphthalenedimethanolYield 97.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A dry 3-neck, 1 L flask equipped with a N2 inlet and dropping funnel is charged with dry THF (200 mL) and LiAlH4 (1.90 g, 0.050 mole). To the stirred mixture is added via the dropping funnel a hot solution of naphthalene-1,4-dicarboxylic acid (4.32 g, 0.020 mole) in THF (200 mL) over a period of about 1 hour. The resulting mixture is stirred without heating for 90 minutes and then is heated to reflux temperature. After 2 hours, additional LiAlH4 (40 mL of a 1.15M solution in THF) is added and refluxing continued for 90 minutes. The reaction is stirred at room temperature overnight, then is quenched carefully with THF-water (3:1), acidified to pH <4 with 2N hydrogen chloride, transferred to a separatory funnel and extracted (3 times) with ether. The combined ether extracts are washed with water (2 times), dried (sodium sulfate), filtered, and concentrated to give a white solid (3.68 g). The solid is crystallized from ethyl acetate-hexane, giving (2.68 g) as white crystals, mp 124°-126° C.

Workup

  1. customA dry 3-neck, 1 L flask equipped with a N2 inlet
  2. temperaturewithout heating for 90 minutes
  3. temperatureis heated
  4. temperatureto reflux temperature
  5. temperaturerefluxing
  6. waitcontinued for 90 minutes
  7. stirringThe reaction is stirred at room temperature overnight
  8. customis quenched carefully with THF-water (3:1)
  9. customtransferred to a separatory funnel
  10. extractionextracted (3 times) with ether
  11. washThe combined ether extracts are washed with water (2 times)
  12. dry with materialdried (sodium sulfate)
  13. filtrationfiltered
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-45a91ad167a749d6bd941cd796568ab0
Source dataset
uspto-grants-1994_11
Patent number
US05360797

Reaction notes

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