Dimethylamine → Vanillin

HRID 1914252Notes

Reaction equation

HRID 1914252 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11]C)[CH:6]=[O:7].CNC>>[OH:11][C:10]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 8419Veratraldehyde

Product 1

HCID 1183VanillinYield 67%

Conditions

Temperature
140 °C

Procedure

A metal autoclave is charged with 14.0 g (84.0 mmol) of 3,4-dimethoxybenzaldehyde and 120 g (1.0 mol) of dimethylamine (40% solution in water). The autoclave is closed and the biphasic reaction mixture is stirred at 140° C. (autogenous pressure 14 bar) for 10 h. Excess dimethylamine and water are removed under reduced pressure, methyl tert-butyl ether is added and the mixture is acidified with 30% hydrochloric acid in water. After phase separation and removal of all volatile constituents of the organic phase, 8.5 g (56.0 mmol, 67% yield) of 4-hydroxy-3-methoxybenzaldehyde are obtained.

Workup

  1. customThe autoclave is closed
  2. customthe biphasic reaction mixture
  3. customExcess dimethylamine and water are removed under reduced pressure, methyl tert-butyl ether
  4. additionis added

Sources & evidence

ORD record
ord-0839d92f618249939d85856b203ca72c
Source dataset
uspto-grants-2013_12
Patent number
US08609903B2

Reaction notes

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