Tetrahydrofuran → HCID 21393733, compound

HRID 461446Notes

Reaction equation

HRID 461446 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]3[C:17]([O:19][C:20](=O)[C:8]=23)=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1>O>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([CH2:17][OH:18])[C:8]=2[CH2:20][OH:19])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2266661-Phenyl-2,3-naphthalenedicarboxylic anhydrideHCID 21226445Aluminium lithium hydride

Product 1

HCID 21393733HCID 21393733, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Phenyl-2,3-naphthalenedicarboxylic anhydride (VII) (25 g) was added to lithium aluminium hydride (10.4 g) in refluxing tetrahydrofuran (500 ml) over 30 min. and the reactants were refluxed for a further 1 hr. Water was added and the precipitate formed was filtered off and washed with ether (3 × 500 ml). The filtrate and the combined ether washings were dried (Mg2SO4) and evaporated to dryness. The residue was recrystallised from toluene to give 1-phenyl-2,3-bis(hydroxymethyl)naphthalene (VIII) m.p. 150°.

Workup

  1. temperaturethe reactants were refluxed for a further 1 hr
  2. customthe precipitate formed
  3. filtrationwas filtered off
  4. washwashed with ether (3 × 500 ml)
  5. dry with materialThe filtrate and the combined ether washings were dried (Mg2SO4)
  6. customevaporated to dryness
  7. customThe residue was recrystallised from toluene

Sources & evidence

ORD record
ord-efe81a96f1524a359dd11025fe73b18c
Source dataset
uspto-grants-1977_12
Patent number
US04062955

Reaction notes

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