Hexamethylenetetramine → p-(Trifluoromethoxy)benzaldehyde

HRID 1701136Notes

Reaction equation

HRID 1701136 reaction equation
C1N2CN3CN(C2)CN1C3.Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1.BrC(Br)C1C=CC([O:32]C(F)(F)F)=CC=1>C(O)C.O>[F:21][C:20]([F:23])([F:22])[O:19][C:16]1[CH:17]=[CH:18][C:13]([CH:12]=[O:32])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 4101HexamethylenetetramineHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzeneHCID 20348560HCID 20348560, compound

Product 1

HCID 69573p-(Trifluoromethoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of hexamethylenetetramine (300 g; 2.14 mole) in ethanol (900 ml) and water (600 ml) a mixture of α-bromo-4-trifluoromethoxytoluene and α,α-dibromo-4-trifluoromethoxytoluene (300 g; 1.11 mole; 76:24 mixture) is added. The reaction mixture is stirred and heated at reflux for 3 hours under a nitrogen atmosphere, and then stirred overnight at room temperature.

Workup

  1. additionis added
  2. temperatureheated
  3. temperatureat reflux for 3 hours under a nitrogen atmosphere
  4. stirringstirred overnight at room temperature

Sources & evidence

ORD record
ord-ef0783f07cd44129be8e6758487105f6
Source dataset
uspto-grants-1980_03
Patent number
US04191768

Reaction notes

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