Hexamethylenetetramine → Benzaldehyde, 4-octyl-

HRID 710365Notes

Reaction equation

HRID 710365 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:27](O)=[O:28]>>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([CH:27]=[O:28])=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 16607Octylbenzene

Product 1

HCID 2734685Benzaldehyde, 4-octyl-Yield 29%

Procedure

A mixture of n-octylbenzene (1.2 g; 6.3 mmol) hexamethylenetetramine (0.97 g; 6.93 mmol) in trifluoroacetic acid was refluxed for 4 h, cooled to room temperature and evaporated to dryness under reduced pressure. The residue was neutralized with 5% NaHCO3 and extracted with diethyl ether (3×5 ml). The combined organic phase was washed with H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane) to give the title compound (0.4 g; 29%) as a colourless oil and starting n-octylbenzene (0.8 g; 67%). 1H-NMR (CDCl3) 0.86 (tr, 3H, J=6.9 Hz); 1.26 (m, 10H); 1.6 (m, 2H); 2.67 (tr, 2H, J=7.9 Hz); 7.31 (d, 2H, J=8.1 Hz); 7.77 (d, 2H, J=8.1 Hz); 9.96 (s, 1H).

Workup

  1. temperaturewas refluxed for 4 h
  2. customevaporated to dryness under reduced pressure
  3. extractionextracted with diethyl ether (3×5 ml)
  4. washThe combined organic phase was washed with H2O, brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure
  8. customthe residue was purified by FCC (SiO2, hexane)

Sources & evidence

ORD record
ord-df640e5e343b484abbc0df706df5820a
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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