1-Naphthaldehyde → HCID 366906, compound

HRID 1059109Notes

Reaction equation

HRID 1059109 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:13]([C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)(=[O:15])[CH3:14].[OH-].[Na+].CCCCCC.C(OCC)(=O)C>CO>[C:1]1([CH:11]=[CH:14][C:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[O:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 61951-NaphthaldehydeHCID 69202-AcetylthiopheneHCID 14798Sodium HydroxideHCID 21226206Ethyl acetate hexane

Product 1

HCID 366906HCID 366906, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.12 g(20 mmol) of 1-naphthaldehyde and 2.52 g(20 mmol) of 2-acetylthiophene were dissolved in 20 ml of methanol and 800 mg(20 mmol) of sodium hydroxide was slowly added thereto. The mixture was reacted at room temperature for 8 hours and then the solid thus produced was filtered and dried. The filtrate was adjusted to pH 4-6 using 1N hydrochloric acid solution and extracted with ethyl acetate. The organic solvent was removed under reduced pressure and the residue was subjected to column chromatography(eluent: hexane/ethyl acetate=4/1, v/v) to give 4.23 g(16 mmol, Yield 80%) of the title compound together with the filtered solid.

Workup

  1. customThe mixture was reacted at room temperature for 8 hours
  2. customthe solid thus produced
  3. filtrationwas filtered
  4. customdried
  5. extractionextracted with ethyl acetate
  6. customThe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ad39b082eb634b098298c8f4be467343
Source dataset
uspto-grants-2003_02
Patent number
US06518429B2

Reaction notes

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