4-dipropylaminomethylbenzyl Alcohol → 4-((Dipropylamino)methyl)benzaldehyde

HRID 1173973Notes

Reaction equation

HRID 1173973 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]>ClCCl.[O-2].[Mn+4].[O-2]>[CH2:1]([N:4]([CH2:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 669412924-dipropylaminomethylbenzyl Alcohol

Product 1

HCID 130230014-((Dipropylamino)methyl)benzaldehydeYield 90.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

The compound (443 mg) obtained in Example 80-2 was dissolved in dichloromethane (9.0 ml) and added with manganese (IV) oxide (chemically treated product, manufactured by Wako Pure Chemical Industries, Ltd.) (873 mg), followed by stirring at room temperature for 5 hours. After completion of the reaction, the solution was filtrated through Celite and the filtrate was then concentrated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (397 mg) as a brown solid.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe solution was filtrated through Celite
  3. concentrationthe filtrate was then concentrated under reduced pressure
  4. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-cf8c7dcd281442d4a285627c1b7e1451
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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