Benzene → HCID 86208125, compound

HRID 1242259Notes

Reaction equation

HRID 1242259 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC=CC=1.[C:17]([NH:21][OH:22])([CH3:20])([CH3:19])[CH3:18]>C(Cl)(Cl)Cl>[C:17]([N+:21]([O-:22])=[CH:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 241BenzeneHCID 7707BenzenepropanalHCID 98586N-tert-butylhydroxylamine

Product 1

HCID 86208125HCID 86208125, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 3-phenylpropionaldehyde (10.0 g, 74.5 mmol, 1.0 equiv) and benzene (150 ml) was added chloroform (25 ml) until a clear solution was obtained. To the clear solution was added N-tert-butylhydroxylamine (7.31 g, 82.0 mmol, 1.1 (equiv) and the resulting mixture was refluxed under nitrogen and Dean-Stark trap for 22 h. Upon cooling oil separated. Oil was separated and product purified by flash chromatography (hexanes: EtOAc=1:1) to give N-tert-butyl-C-(2-phenylethyl)nitrone (7.31 g, 45.1%) as a light color oil: 1H NMR (CD3OD) δ 7.30–7.27 (m, 2H, Ar—H), 7.23–7.19 (m, 3H, Ar—H), 6.80 (t, 1H, Ar—H), 2.77–2.62 (m, 4H, 2CH2), 1.46 (s, 9H, t-Bu).

Workup

  1. customwas obtained
  2. temperaturethe resulting mixture was refluxed under nitrogen
  3. temperatureUpon cooling oil
  4. customseparated
  5. customOil was separated
  6. customproduct purified by flash chromatography (hexanes: EtOAc=1:1)

Sources & evidence

ORD record
ord-a43e99036eeb4103990287a9d15ae2d7
Source dataset
uspto-grants-2006_10
Patent number
US07115666B2

Reaction notes

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