Dimethylamine → 3-[(Dimethylamino)methyl]-4-hydroxy-5-methoxybenzaldehyde

HRID 1714692Notes

Reaction equation

HRID 1714692 reaction equation
[CH3:1][NH:2][CH3:3].[CH2:4]=O.[CH3:6][O:7][C:8]1[CH:13]=[C:12]([CH:14]=[O:15])[CH:11]=[CH:10][C:9]=1[OH:16]>C(O)C>[CH3:1][N:2]([CH2:4][C:10]1[CH:11]=[C:12]([CH:13]=[C:8]([O:7][CH3:6])[C:9]=1[OH:16])[CH:14]=[O:15])[CH3:3]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 1183Vanillin

Product 1

HCID 14877773-[(Dimethylamino)methyl]-4-hydroxy-5-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

18.0 g (0.15 mol) of a 40% aqueous dimethylamine solution were added to 12.0 g (0.15 mol) of a 37% aqueous formaldehyde solution in 90 ml of ethanol. Then 15.2 g (0.10 mol) of 4-hydroxy-3-methoxybenzaldehyde (vanillin) were added. The reaction mixture was refluxed for 30 minutes and stirred for a further 24 hours at room temperature. Then the reaction mixture was left to stand overnight in the refrigerator at 0 to 5° C. The precipitated solid was filtered out, washed with ice-cold acetone and dried. The result was a white powder.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. waitThen the reaction mixture was left
  3. waitto stand overnight in the refrigerator at 0 to 5° C
  4. filtrationThe precipitated solid was filtered out
  5. washwashed with ice-cold acetone
  6. customdried

Sources & evidence

ORD record
ord-37f91b1c96af4a438247721fd294bafc
Source dataset
uspto-grants-2010_09
Patent number
US07799096B2

Reaction notes

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