Benzaldehyde → HCID 11807110, compound

HRID 1621158Notes

Reaction equation

HRID 1621158 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9]/[N:10]=[C:11](\[CH3:20])/[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O>Cl.O1CCOCC1>[CH3:20][C:11]1[N+:10]([O-:9])=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:8][C:12]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 95660631-Phenyl-1,2-propanedione-2-oxime

Product 1

HCID 11807110HCID 11807110, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of benzaldehyde (325 mg, 311 μL, 3.06 mmol) in HCl (4M in dioxane, 10 mL was added (E)-2-(hydroxyimino)-1-phenylpropan-1-one (500 mg, 3.06 mmol) at 0-5° C. The ice bath was removed and the mixture was stirred at RT for 24 h. All volatiles were removed and the residue was dissolved in HCl (4M in dioxane, 10 mL). The reaction mixture was stirred at RT for 6 h and concentrated. The obtained suspension was filtered, washed with diethyl ether and dried in vacuo to give the product as colorless solid (398 mg, 1.58 mmol, 51.7%).

Workup

  1. customThe ice bath was removed
  2. customAll volatiles were removed
  3. dissolutionthe residue was dissolved in HCl (4M in dioxane, 10 mL)
  4. stirringThe reaction mixture was stirred at RT for 6 h
  5. concentrationconcentrated
  6. filtrationThe obtained suspension was filtered
  7. washwashed with diethyl ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-bfeeaac0ee914a47a3590a8951145700
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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