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

HRID 2269227

Reaction equation

HRID 2269227 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[C:8]1([C:14]([C:17]2[CH:22]=[CH:21]C=[CH:19][CH:18]=2)([CH3:16])[CH3:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1N2CN3CN(C2)CN1C3>>[CH3:16][C:14]([C:17]1[CH:22]=[CH:21][C:2]([CH:3]=[O:5])=[CH:19][CH:18]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:15]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 13065Dimethyldiphenylmethane

Product 1

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

Procedure

Trifluoroacetic acid (35 ml), was mixed with 3.93 g(20.0 mmol), of 2,2-diphenylpropane and 2.80 g (20.0 mmol), of hexamethylenetetramine and heated to reflux for 16 hours. After cooling to room temperature, the reaction mixture was poured into ice water and the mixture was stirred for 1 hour. The solution was adjusted to pH=about 9 and extracted with 100 ml of diethyl ether. The organic extract was washed with saturated saline and dried with sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to obtain 3.61 g (yield: 80.5%), of the target compound as a pale yellow oily substance.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. extractionextracted with 100 ml of diethyl ether
  4. extractionThe organic extract
  5. washwas washed with saturated saline
  6. dry with materialdried with sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)
  9. customto obtain 3.61 g (yield: 80.5%)

Sources & evidence

ORD record
ord-27f16714ee9f40f4a690c202074ef496
Source dataset
uspto-grants-2001_12
Patent number
US06329399B1

Linked notes

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