Hydrochloric Acid → 3-Methyl-3-phenylbutan-2-one

HRID 1773908Notes

Reaction equation

HRID 1773908 reaction equation
CON(C)[C:4](=[O:14])[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH3:6].[Li]C.[CH3:18]COCC.Cl>C1COCC1>[CH3:6][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[C:4](=[O:14])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 59788661N-Methoxy-N-methyl-2-phenyl-isobutyramideHCID 178418348HCID 178418348, compound

Product 1

HCID 2854623-Methyl-3-phenylbutan-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methoxy-N-methyl-2-phenyl-isobutyramide (example 207E) (16 g, 77.2 mmoles) in THF (300 mL) cooled at −50° C. is added dropwise a 1.6M solution of MeLi in Et2O (80 mL, 131.2 mmoles). The reaction mixture is allowed to reach 0° C. and 1N HCl (130 mL, 130 mmoles) is added. The aqueous phase is extracted with Et2O. The organic phase is washed with brine, dried over MgSO4, filtered and the solvent is removed under reduced pressure to give 3-methyl-3-phenyl-butan-2-one.

Workup

  1. customto reach 0° C.
  2. extractionThe aqueous phase is extracted with Et2O
  3. washThe organic phase is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-df5282149dc0482aa6d17b1b3e2c6c34
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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