[4-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]phenyl]methanol → 4-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]benzaldehyde

HRID 85250Notes

Reaction equation

HRID 85250 reaction equation
[CH2:1]([N:5]([CH2:24][CH2:25][CH2:26][CH3:27])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=2)=[C:8]([O:22][CH3:23])[CH:7]=1)[CH2:2][CH2:3][CH3:4]>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:24]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[CH:15]=[CH:16][C:17]([CH:20]=[O:21])=[CH:18][CH:19]=2)=[C:8]([O:22][CH3:23])[CH:7]=1)[CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 1

HCID 68009291[4-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]phenyl]methanol

Product 1

HCID 866675494-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]benzaldehydeYield 67.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In 60 ml of dichloromethane was dissolved 2.28 g (6.2 mmol) of [4-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]phenyl]methanol, and 10.8 g of active manganese dioxide was added thereto. The mixture was stirred at room temperature for 18 hours. After the reaction mixture was filtrated and concentrated, the residue was dissolved in 170 ml of ether, 80 mg of iodine pieces were added thereto, and the mixture was stirred. The reaction mixture was washed with a 5% sodium bisulfite solution and then with a saturated saline solution, and dried over anhydrous magnesium sulfate. After ether was evaporated off, the residue was purified by silica gel column chromatography to give 1.54 g of an orange oily matter (yield: 67.9%).

Workup

  1. additionwas added
  2. filtrationAfter the reaction mixture was filtrated
  3. concentrationconcentrated
  4. dissolutionthe residue was dissolved in 170 ml of ether
  5. addition80 mg of iodine pieces were added
  6. stirringthe mixture was stirred
  7. washThe reaction mixture was washed with a 5% sodium bisulfite solution
  8. dry with materialwith a saturated saline solution, and dried over anhydrous magnesium sulfate
  9. customAfter ether was evaporated off
  10. customthe residue was purified by silica gel column chromatography
  11. customto give 1.54 g of an orange oily matter (yield: 67.9%)

Sources & evidence

ORD record
ord-a057d088ab9a476c97cc0c1863eef72f
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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