1-(2,5-Dimethoxyphenyl)prop-2-en-1-ol → 2,5-Dimethoxyphenyl vinyl ketone

HRID 1109614Notes

Reaction equation

HRID 1109614 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]([CH:13]=[CH2:14])[OH:12]>C(Cl)Cl.O=[Mn]=O>[CH:13]([C:11]([C:4]1[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[O:12])=[CH2:14]

Participants

4

Reactant 1

HCID 190210221-(2,5-Dimethoxyphenyl)prop-2-en-1-ol

Product 1

HCID 127134602,5-Dimethoxyphenyl vinyl ketone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

Activated MnO2 (100 g) was added in portions to a mechanically stirred solution of 2,5-dimethoxyphenyl vinyl carbinol (12.5 g, 0.064 mole) in 250 ml of methylene chloride. The mixture was stirred at room temperature for 24 hours and then filtered through a patch of Celite. The filtrate was concentrated to give a brown oil which was purified by column chromatography on silica gel, using diethyl ether/hexane (1/1) as eluant. The compound was obtained as a light brown oil; 7.2 g; IR (neat) 1680 cm-1 ; NMR (CDCl3) δ6.85-7.1 (m, 4H); 6.3 (d, 1H); 5.8 (d, 1H); 3.8 and 3.85 (two singlets, 6H).

Workup

  1. filtrationfiltered through a patch of Celite
  2. concentrationThe filtrate was concentrated
  3. customto give a brown oil which
  4. customwas purified by column chromatography on silica gel
  5. customThe compound was obtained as a light brown oil

Sources & evidence

ORD record
ord-bdea4ccc92574d80866c9ad938bf56eb
Source dataset
uspto-grants-1994_06
Patent number
US05321141

Reaction notes

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