Hydrochloric Acid → 2-(Hydroxyimino)-1-phenylbutan-1-one

HRID 2377962Notes

Reaction equation

HRID 2377962 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[N:12](OC(C)(C)C)=[O:13].Cl>O1CCCC1>[C:6]1([C:1](=[O:5])[C:2](=[N:12][OH:13])[CH2:3][CH3:4])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10315ButyrophenoneHCID 10906Tert-Butyl nitrite

Product 1

HCID 713398922-(Hydroxyimino)-1-phenylbutan-1-oneYield 56.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the butyrophenone (300 mg, 2.0 mmol) in tetrahydrofuran (8 mL) was added t-butyl nitrite (0.475 mL, 4.0 mmol) and hydrochloric acid (4N in dioxane, 0.65 mL, 2.6 mmol). The reaction was stirred at RT for 3 hours, then the solvent was evaporated and the residue was purified by Prep HPLC (ammonium acetate/water/acetonitrile) to give the title material (0.200 g, 56%). HPLC 91% (220 nm), LCMS (+ESI, M+H+) m/z 178; 1H NMR (400 MHz, methanol-d4) δ (ppm): 1.13 (3H, t, J=7.6 Hz), 2.71 (2H, qa, J=7.6 Hz), 7.45 (2H, br t), 7.57 (1H, br t), 7.90 (2H, d, J=7.0 Hz).

Workup

  1. customthe solvent was evaporated
  2. customthe residue was purified by Prep HPLC (ammonium acetate/water/acetonitrile)

Sources & evidence

ORD record
ord-c65e26bfad6e4567be696c2c75ffd998
Source dataset
uspto-grants-2008_12
Patent number
US07470713B2

Reaction notes

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