1-Naphthaldehyde → 37630-26-5

HRID 1635945Notes

Reaction equation

HRID 1635945 reaction equation
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].[N+:18]([CH3:21])([O-:20])=[O:19].C(OC(=O)C)C>CCCCCC>[N+:18](/[CH:21]=[CH:11]/[C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 61951-NaphthaldehydeHCID 6375NitromethaneHCID 8857Ethyl AcetateHCID 517165Ammonium Acetate

Product 1

HCID 538167937630-26-5Yield 62%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

7.81 g (50 mmol) of 1-naphthaldehyde and 1.54 g (20 mmol) of ammonium acetate were added to 70 ml of nitromethane and heated under reflux for 3 hours (see: J. Org. Chem., 1984, 49, 4761). 100 ml of ethylacetate was added and the resulting mixture was washed with 50 ml of water and 50 ml of brine. The organic layer was collected and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was subjected to column chromatography (eluent: hexane/ethylacete=90/10, v/v) to give 6.27 g( 0.031 mmol, Yield 62%) of the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours (see: J. Org. Chem., 1984, 49, 4761)
  3. washthe resulting mixture was washed with 50 ml of water and 50 ml of brine
  4. customThe organic layer was collected
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-536971e4e6074feaa6d8340e274fbb76
Source dataset
uspto-grants-2003_01
Patent number
US06511978B1

Reaction notes

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