Water → 1,8-Naphthalenedimethanol

HRID 1503405Notes

Reaction equation

HRID 1503405 reaction equation
[C:1]1(=O)[C:10]2[C:5]3[C:6](=[CH:11][CH:12]=[CH:13][C:4]=3[C:3](=[O:14])[O:2]1)[CH:7]=[CH:8][CH:9]=2.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[OH:2][CH2:1][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:5]=1[C:4]([CH2:3][OH:14])=[CH:13][CH:12]=[CH:11]2

Participants

6

Reactant 4

HCID 962WaterHCID 6693Naphthalic anhydrideHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

Product 1

HCID 748461,8-Naphthalenedimethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Benzo[de]isochromene-1,3-dione (30 g, 0.15 mol) in anhydrous THF (300 mL) was added dropwise to a solution of LAH (10 g, 0.38 mol) in anhydrous THF (200 mL). The result reaction mixture was refluxed for 3 h, then allowed to cool and stand overnight at room temperature. Water and 10% aq. NaOH was added dropwise, filtered. The filtrate was concentrated in vacuum to give the crude product, which was used directly without purification (1.15 g, crude). 1H-NMR (CDCl3): 5.06 (m, 4H), 5.23 (m, 2H), 7.42 (m, 2H), 7.60 (m, 2H), 7.82 (m, 2H).

Workup

  1. customThe result reaction mixture
  2. temperaturewas refluxed for 3 h
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuum

Sources & evidence

ORD record
ord-b2bdb07bd83e4979a70d6db3e27ff212
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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