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

HRID 1356845

反応式

HRID 1356845 の反応式
[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]

参加物

5

反応物 4

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 13065Dimethyldiphenylmethane

生成物 1

HCID 185094134-(2-Phenylpropan-2-yl)benzaldehyde収率 80.5%

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-171e9a76dd6b4c21b461fd0b5c16f2f9
出典データセット
uspto-grants-2003_07
特許番号
US06586633B1

関連ノート

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