Phenylacetaldehyde → HCID 315883, compound

HRID 1242269Notes

Reaction equation

HRID 1242269 reaction equation
[C:1]1([CH2:7][CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([NH:14][OH:15])([CH3:13])([CH3:12])[CH3:11]>Cl.C(Cl)(Cl)Cl>[C:10]([N+:14]([O-:15])=[CH:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 998PhenylacetaldehydeHCID 98586N-tert-butylhydroxylamine

Product 1

HCID 315883HCID 315883, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6212ChloroformSolvent

Procedure

To a mixture of phenyl-acetaldehyde (1.20 g, 10.00 mmol) and chloroform (50 ml) was added N-tert-butylhydroxylamine (1.07 g, 12.00 mmol) followed by 5 drops of conc. HCl. The mixture was stirred at rt for 18 h. The mixture was concentrated under vacuum to give an oil. The residue was purified by column chromatography (hexane:EtOAc=1:1) followed by EtOAc to give the title compound as a white solid: Yield: 80%, m.p. 143° C.: 1H NMR (CDCl3) δ 7.38 (m, 5H), 6.90 (s, 1H), 4.95 (dd, 2H), 1.25 (s, 9H).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customto give an oil
  3. customThe residue was purified by column chromatography (hexane:EtOAc=1:1)

Sources & evidence

ORD record
ord-8e99964f836d4f3a890d4fd8455f9819
Source dataset
uspto-grants-2006_10
Patent number
US07115666B2

Reaction notes

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