Hexamethylenetetramine → 2,3,4,5-Tetramethoxy-6-methylbenzaldehyde

HRID 1292019Notes

Reaction equation

HRID 1292019 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([O:10][CH3:11])=[C:5]([O:12][CH3:13])[C:4]=1[O:14][CH3:15].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:28](O)=[O:29]>>[CH3:1][O:2][C:3]1[C:4]([O:14][CH3:15])=[C:5]([O:12][CH3:13])[C:6]([O:10][CH3:11])=[C:7]([CH3:9])[C:8]=1[CH:28]=[O:29]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 98777642,3,4,5-Tetramethoxytoluene

Product 1

HCID 148523342,3,4,5-Tetramethoxy-6-methylbenzaldehydeYield 90%

Procedure

To a solution of 1,2,3,4-tetramethoxy-5-methylbenzene (34.3 g, 162 mmol) in trifluoroacetic acid (200 ml) was added hexamethylenetetramine (25.0 g, 178 mmol), and the solution was heated under reflux for 3 hours. The solvent was distilled off under reduced pressure. Water (200 ml) was added to the residue which was then heated under reflux for one hour, neutralized with 3N sodium hydroxide and extracted with ethyl acetate (200 ml×3), and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography to give 34.9 g of the title compound.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 3 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionWater (200 ml) was added to the residue which
  5. temperaturewas then heated
  6. temperatureunder reflux for one hour
  7. extractionextracted with ethyl acetate (200 ml×3)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-10a70d8b74e24136b718b383b7341e05
Source dataset
uspto-grants-1998_05
Patent number
US05756475

Reaction notes

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