4'-Methoxyacetophenone → 1-(4-Methoxyphenyl)butane-1,3-dione

HRID 2300604Notes

Reaction equation

HRID 2300604 reaction equation
[C:1]1([C:7](=[O:13])[CH2:8][C:9](=[O:12])[CH2:10]C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][O:15]C1C=CC(C(=O)C)=CC=1>CCOC(C)=O>[CH3:14][O:15][C:4]1[CH:3]=[CH:2][C:1]([C:7](=[O:13])[CH2:8][C:9](=[O:12])[CH3:10])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 74764'-MethoxyacetophenoneHCID 21408Propionyl Acetophenone

Product 1

HCID 776401-(4-Methoxyphenyl)butane-1,3-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared (as described above for Intermediate 16) from 3.0 g of 4′-methoxyacetophenone and 3.95 mL of EtOAc. Purification by recrystallization from toluene/hexane afforded the title compound: 1H NMR (400 MHz, CDCl3, enol form) δ7.70 (d, 2H, J=8.20), 7.34 (d, 2H, J=8.20), 6.17 (s, 1H), 3.87 (s, 3H), 2.17 (s, 3H); low resolution MS (ES)m/e 193.1 (MH+)

Workup

  1. customPurification
  2. customby recrystallization from toluene/hexane

Sources & evidence

ORD record
ord-51db3def171d4800ab3da4f2de01dc2f
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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