Propionyl Acetophenone → 1(4-Isopropoxyphenyl)-1,3-butanedione

HRID 2300607Notes

Reaction equation

HRID 2300607 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.[CH:14]([O:17]C1C=CC(C(=O)C)=CC=1)([CH3:16])[CH3:15]>CCOC(C)=O>[CH:14]([O:17][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)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 21408Propionyl AcetophenoneHCID 7340081-(4-(Propan-2-yloxy)phenyl)ethan-1-one

Product 1

HCID 183763601(4-Isopropoxyphenyl)-1,3-butanedione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared (as described above for Intermediate 16) from 2.42 g of 4′-isopropoxyacetophenone and 2.65 mL of EtOAc to yield 2.25 grams of Intermediate 29: TLC analysis: Rf=0.73 (2/1, hexanes/EtOAc); 1H NMR (400 MHz, CDCl3, enol form) δ7.84 (d, 2H, J=8.9), 6.9 (d, 2H, J=9.0), 6.1 (s, 1H), 4.62 (hept, 1H, J=6.0), 2.16 (s, 3H), 1.36 (d, 6H, J=6.0).

Sources & evidence

ORD record
ord-527aea3ddca6444ab88a6ae7bc6d2d6e
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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