2-(3,4-Dimethoxyphenyl)-1,4-pentadien-3-ol → 2-(3,4-Dimethoxyphenyl)-1,4-pentadien-3-one

HRID 733425Notes

Reaction equation

HRID 733425 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH:13]([OH:16])[CH:14]=[CH2:15])=[CH2:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>O=[Mn]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13](=[O:16])[CH:14]=[CH2:15])=[CH2:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

3

Reactant 1

HCID 578407572-(3,4-Dimethoxyphenyl)-1,4-pentadien-3-ol

Product 1

HCID 578407652-(3,4-Dimethoxyphenyl)-1,4-pentadien-3-oneYield 56.6%

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

According to the General Procedure B, MnO2 (1.81 g, 20.79 mmol) and 2-(3,4-dimethoxyphenyl)-1,4-pentadien-3-ol (220 mg, 0.99 mmol) are converted to give after workup and chromatography (SiO2, PE/EE=2:1, Rf=0.40) the title compound (122 mg, 0.56 mmol, 56%) as a yellow oil; C14H16O3 (218.25).

Sources & evidence

ORD record
ord-2f95d910c0f841c983a09594a6057562
Source dataset
uspto-grants-2009_09
Patent number
US07589205B2

Reaction notes

Loading…