Dimethylamine → Syringaldehyde

HRID 1914253Notes

Reaction equation

HRID 1914253 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11]C)[CH:6]=[O:7].CNC>>[OH:11][C:10]1[C:9]([O:13][CH3:14])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 68583,4,5-Trimethoxybenzaldehyde

Product 1

HCID 8655SyringaldehydeYield 72%

Conditions

Temperature
140 °C

Procedure

A 100 ml glass autoclave is charged with 11.8 g (60.0 mmol) of 3,4,5-trimethoxybenzaldehyde and 47.2 g (420 mmol) of dimethylamine (40% solution in water). The autoclave is closed and the biphasic reaction mixture is stirred at 140° C. (autogenous pressure 10 bar) for 18 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, 4-hydroxy-3,5-dimethoxybenzaldehyde is obtained in a yield of 72%.

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
  5. customAfter phase separation and removal of all volatile constituents of the organic phase

Sources & evidence

ORD record
ord-aad75d8fd1ef45cb9c299117dcff6371
Source dataset
uspto-grants-2013_12
Patent number
US08609903B2

Reaction notes

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