2-Phenylacetophenone → 1,2-Diphenyl-1-ethanone oxime

HRID 343089

Reaction equation

HRID 343089 reaction equation
[C:1]1([C:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:17][OH:18].O.O.O.C([O-])(=O)C.[Na+]>C(O)C.O>[C:1]1([C:7](=[N:17][OH:18])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 99482-PhenylacetophenoneHCID 443297Hydroxyamine hydrochlorideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 2353831,2-Diphenyl-1-ethanone oximeYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of deoxybenzoin (407.4 g, 2.076 mol) in 2 L of absolute ethanol and 600 mL of water was treated with hydroxylamine hydrochloride (288 g, 4.15 mol) and sodium acetate trihydrate (564 g, 4.15 mol). The solution was then warmed to reflux for 2 hours. The reaction mixture was then diluted with 1000 mL of 30% aqueous ethanol and allowed to cool to room temperature whereupon crystals of pure oxime formed which were isolated by filtration and air dried to afford 415.4 g, 95%, mp 94°-96° C. of pure deoxybenzoin oxime.

Workup

  1. temperatureThe solution was then warmed
  2. temperatureto reflux for 2 hours
  3. customformed which
  4. customwere isolated by filtration and air
  5. customdried

Sources & evidence

ORD record
ord-bd13a5f5f72e4db9ba33ba95fdd8b9fb
Source dataset
uspto-grants-1999_01
Patent number
US05859257

Linked notes

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