Benzaldehyde → HCID 178515616, compound

HRID 448153Notes

Reaction equation

HRID 448153 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH:13](=[N:1]/[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2)\[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 83588-Amino-2-naphthalenolHCID 24436Sodium Sulfate

Product 1

HCID 178515616HCID 178515616, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8-amino-2-naphthol 1 (8.2 g, 52 mmol), benzaldehyde (16 mL, 156 mmol) and sodium sulfate (41.3 g, 291 mmol) in THF (100 mL) was stirred at reflux over night. The mixture was cooled to room temperature, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography (hexane/ethyl acetate/triethyl amine 75/23/2) to give 12.65 g of impure (E)-8-(benzylideneamino)naphthalen-2-ol (2) which was used in the next step without further purification.

Workup

  1. temperatureat reflux over night
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography (hexane/ethyl acetate/triethyl amine 75/23/2)

Sources & evidence

ORD record
ord-34e6e41b3c554321906c8ad125c82f86
Source dataset
uspto-grants-2013_07
Patent number
US08481581B2

Reaction notes

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