Hexamethylenetetramine → 4-(2-Phenylpropan-2-yl)benzaldehyde

HRID 1356845

Reaction equation

HRID 1356845 reaction equation
[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:28](O)=[O:29].C(=O)([O-])[O-].[K+].[K+]>>[CH3:8][C:7]([C:10]1[CH:11]=[CH:12][C:13]([CH:28]=[O:29])=[CH:14][CH:15]=1)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:9]

Participants

5

Reactant 4

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 13065Dimethyldiphenylmethane

Product 1

HCID 185094134-(2-Phenylpropan-2-yl)benzaldehydeYield 80.5%

Procedure

2,2-Diphenylpropane (3.93 g; 20.0 mmol) and hexamethylenetetramine (2.80 g; 20.0 mmol) were added to trifluoroacetic acid (35 ml), and the mixture was refluxed for 16 hours. The mixture was brought to room temperature, and poured into ice/water, followed by stirring for 1 hour. The pH of the mixture was adjusted to about 9 with potassium carbonate, followed by extraction with ether (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to thereby yield 3.61 g of the target compound (yield: 80.5%).

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. customwas brought to room temperature
  3. extractionfollowed by extraction with ether (100 ml)
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-171e9a76dd6b4c21b461fd0b5c16f2f9
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Linked notes

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