Hexamethylenetetramine → 4-Nonylbenzaldehyde

HRID 1492086

Reaction equation

HRID 1492086 reaction equation
C1N2CN3CN(C2)CN1C3.[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.FC(F)(F)[C:28](O)=[O:29]>>[CH2:17]([C:11]1[CH:16]=[CH:15][C:14]([CH:28]=[O:29])=[CH:13][CH:12]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 14126n-Nonylbenzene

Product 1

HCID 109333644-NonylbenzaldehydeYield 57%

Conditions

Temperature
25 °C

Procedure

Oxidative Formylation--Allow a two-phase mixture of trifluoroacetic acid (150 mL) and hexamethylene tetramine (14.0 g, 0.100 mol), and 1-phenyl-n-nonane (20.4 g, 0.100 mol) to stand 18 hrs. at 25° C., and then reflux for 22 hrs. Concentrate the homogenous reaction mixture and pour the residue over ice and H2O (total of 600 mL). Add diethyl ether (200 mL) and stir the mixture vigorously for 30 min. Raise the pH of the mixture to pH 8 with solid Na2CO3, and add diethyl ether (200 mL). Shake the layers and separate. Extract the aqueous phase with diethyl ether. Wash the combined organic solutions with H2O and brine, dry and filter. Evaporate the solvent, and distill the residue to give 4-(n-nonyl)benzaldehyde (57% yield, 13.2 g) b.p. 136°-139° C. at 0.55 mm.

Workup

  1. concentrationConcentrate the homogenous reaction mixture
  2. additionpour the residue over ice and H2O (total of 600 mL)
  3. temperatureRaise the pH of the mixture to pH 8 with solid Na2CO3
  4. additionadd diethyl ether (200 mL)
  5. customShake the layers and separate
  6. extractionExtract the aqueous phase with diethyl ether
  7. washWash the combined organic solutions with H2O and brine
  8. customdry
  9. filtrationfilter
  10. customEvaporate the solvent
  11. distillationdistill the residue

Sources & evidence

ORD record
ord-859f6f1e6fac4fc288830c849b4579ba
Source dataset
uspto-grants-1994_12
Patent number
US05371284

Linked notes

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