Benzaldehyde → HCID 3236994, compound

HRID 2194293Notes

Reaction equation

HRID 2194293 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9]/[C:10](/[C:13]([CH3:15])=O)=[N:11]\[OH:12].Cl.[OH-].[Na+]>C(O)(=O)C>[CH3:9][C:10]1[N+:11]([O-:12])=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:8][C:13]=1[CH3:15]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 64096332,3-Butanedione monoxime

Product 1

HCID 3236994HCID 3236994, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

500 g of benzaldehyde and 476 g of diacetylmonoxime were suspended in 1 L of acetic acid and cooled in an ice bath. At internal temperature of 7° C., hydrochloride gas is slowly blown in to be saturated. At room temperature, the mixture was stirred overnight. The reaction mixture was poured into 1.5 kg of ice, and neutralized with 25% sodium hydroxide solution. The crystalline precipitate was isolated by filtration and washed with 1 L of water and 1 L of diisopropylether. The obtained crystals were dissolved in 3 L of chloroform and insoluble matter was filtered off. The filtrate was dried with 200 g of anhydrous sodium sulfate, filtered, and the filtrate was concentrated in vacuo. 3 L of IPE was added to the residue to be crystallized, the crystal was isolated by filtration, dried under reduced pressure at 50° C. for 1 hour, and 440 g of the subject compound was prepared.

Workup

  1. temperaturecooled in an ice bath
  2. customThe crystalline precipitate was isolated by filtration
  3. washwashed with 1 L of water and 1 L of diisopropylether
  4. dissolutionThe obtained crystals were dissolved in 3 L of chloroform
  5. filtrationinsoluble matter was filtered off
  6. dry with materialThe filtrate was dried with 200 g of anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated in vacuo
  9. addition3 L of IPE was added to the residue
  10. customto be crystallized
  11. customthe crystal was isolated by filtration
  12. customdried under reduced pressure at 50° C. for 1 hour

Sources & evidence

ORD record
ord-a99d85b9e0d74436bdfff33aacdda4f2
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

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