Hydrochloric Acid → 1-Phenyl-2-hexanone

HRID 1958557Notes

Reaction equation

HRID 1958557 reaction equation
CON(C)[C:4](=[O:9])[CH2:5][CH2:6][CH2:7][CH3:8].[CH2:11]([Mg]Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>C1COCC1>[C:12]1([CH2:11][C:4](=[O:9])[CH2:5][CH2:6][CH2:7][CH3:8])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3801384N-methoxy-N-methylpentanamideHCID 178418336HCID 178418336, compound

Product 1

HCID 331911-Phenyl-2-hexanoneYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part B: To a magnetically stirred solution of pentanoic acid methoxy-methyl-amide (8.6 g, 59.3 mmol) at 0° C. in anhydrous THF (100 ml) was slowly added benzylmagnesium chloride (2 M solution in THF, 45 ml, 90 mmol) and the resulting mixture was reacted for 20 hours in a nitrogen atmosphere at room temperature. The reaction mixture was poured in excess of a cold (0° C.) aqueous hydrochloric acid (4 N solution) and extracted with MTBE. The organic layer was dried over Na2SO4, filtered and concentrated to give crude product. This crude product was further purified using Sepacore equipment: Gradient: (petroleum ether/diethyl ether=98/2 (v/v))=>(petroleum ether/diethyl ether=95/5 (v/v)) to give 1-phenylhexan-2-one (Intermediate II-1) (7.38 gram, 71% yield) as a colorless oil; 1H-NMR (400 MHz, CDCl3) δ 0.86 (t, J=7, 3H), 1.21-1.31 (m, 2H), 1.48-1.58 (m, 2H), 2.41-2.47 (m, 2H), 3.68 (s, 2H), 7.18-7.36 (m, 5H).

Workup

  1. customat 0° C.
  2. customthe resulting mixture was reacted for 20 hours in a nitrogen atmosphere at room temperature
  3. extractionextracted with MTBE
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give crude product
  8. customThis crude product was further purified

Sources & evidence

ORD record
ord-15e260e5904342128acedaeeb1602ffa
Source dataset
uspto-grants-2013_04
Patent number
US08410135B2

Reaction notes

Loading…