Diphenylacetaldehyde → HCID 73185975, compound

HRID 914979Notes

Reaction equation

HRID 914979 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:17][OH:18].[OH-].[Na+]>CCO>[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[N:17][OH:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 13696DiphenylacetaldehydeHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 73185975HCID 73185975, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of diphenylacetaldehyde (51) (4.0 g, 20.3 mmol) in EtOH (50 mL) were sequentially added hydroxylamine hydrochloride (1.41 g, 20.3 mmol) and 2 N NaOH (aq. 5 mL). The reaction was stirred at room temperature overnight followed by removal of EtOH under reduced pressure. The residue was washed with water (50 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to give 52 (4.0 g, 93%).

Workup

  1. customfollowed by removal of EtOH under reduced pressure
  2. washThe residue was washed with water (50 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2ab30e63bb4c4639aa3e77045827df6f
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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