2-Naphthol → HCID 19069389, compound

HRID 128804Notes

Reaction equation

HRID 128804 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[H-].[Na+].F[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1>CN(C=O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 86632-NaphtholHCID 24758Sodium hydrideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 19069389HCID 19069389, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-naphthol (14.4 g) in DMF (100 ml) is added sodium hydride (4.2 g of 60% dispersion). When gas evolution ceases, 4-fluorobenzaldehyde (11.5 ml) is added, and the reaction mixture is stirred at 130° for 48 hr. The mixture is cooled, poured onto crushed ice, and the product extracted with ether. Chromatography of the concentrated extract with 3:2 dichloromethane-hexane provides 4-(2-naphthyloxy)benzaldehyde as a pale yellow solid (10.25 g, 41%).

Workup

  1. temperatureThe mixture is cooled
  2. additionpoured
  3. customonto crushed ice
  4. extractionthe product extracted with ether
  5. extractionChromatography of the concentrated extract with 3:2 dichloromethane-hexane

Sources & evidence

ORD record
ord-92c296032d8e4472afd38d24961949d2
Source dataset
uspto-grants-1995_11
Patent number
US05464865

Reaction notes

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