Dimethylamine → 4-Hydroxybenzaldehyde

HRID 1914251Notes

Reaction equation

HRID 1914251 reaction equation
C[O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.CNC>>[OH:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 312444-Methoxybenzaldehyde

Product 1

HCID 1264-HydroxybenzaldehydeYield 81%

Conditions

Temperature
140 °C

Procedure

A 100 ml glass autoclave is charged with 8.84 g (65.0 mmol) of 4-methoxybenzaldehyde and 51.2 g (455 mmol) of dimethylamine (40% solution in water). The autoclave is closed and the biphasic reaction mixture is stirred at 140° C. (autogenous pressure 7.5 bar) for 15 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, 6.5 g (0.53 mmol, 81% yield) of 4-hydroxybenzaldehyde 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-432db09b34b34a088c8964378facdde5
Source dataset
uspto-grants-2013_12
Patent number
US08609903B2

Reaction notes

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