Ethylenediamine → Decanal

HRID 1488791Notes

Reaction equation

HRID 1488791 reaction equation
C(O)(C)(C)C.C(N(C)[C:14](=[O:24])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])C1C=CC=CC=1.C(N)CN.[Li]>C(N)CC.O>[CH:14](=[O:24])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 6386tert-Butanol2×HCID 3028194LithiumHCID 11300336HCID 11300336, compound

Product 1

HCID 8175DecanalYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7852PropylamineSolvent2×

Procedure

n-Propylamine solution with t-butanol. A solution of N-benzyl-N-methyldecanoic acid amide (10 g, 0.036 mol) in n-propylamine (100 mL), ethylenediamine (13 g, 0.216 mol) and t-butanol (16 g, 0.216 mol) was cooled to -18° and lithium (1.77 g, 0.252 mol), in small pieces, was added rapidly. After 15 min, the temperature raised to 12° and then lowered. After another 45 min, the reaction turned blue and after another 30 min a yellow solution was obtained. The reaction mixture was poured over 75 g of crushed ice and water (75 mL). The mixture was extracted with ether (2×75 mL) and the combined ether extracts were washed with brine (2×50 mL). The ether was evaporated and the residue was dissolved in THF (50 mL) and 3N hydrochloric acid (15 mL). The solution was heated under reflux for 2 hr and then cooled and diluted with brine (50 mL). The mixture was extracted with ether (2×75 mL) and the combined ether extracts were washed with brine (1×50 mL) and filtered through 1PS filter paper. The ether was evaporated and the residue was distilled to give 2.0 g (36%) of n-decanal having a bp 100°-105° (15 mm).

Workup

  1. temperaturethe temperature raised to 12°
  2. waitAfter another 45 min
  3. waitthe reaction turned blue and after another 30 min
  4. customa yellow solution was obtained
  5. extractionThe mixture was extracted with ether (2×75 mL)
  6. washthe combined ether extracts were washed with brine (2×50 mL)
  7. customThe ether was evaporated
  8. dissolutionthe residue was dissolved in THF (50 mL)
  9. temperatureThe solution was heated
  10. temperatureunder reflux for 2 hr
  11. temperaturecooled
  12. additiondiluted with brine (50 mL)
  13. extractionThe mixture was extracted with ether (2×75 mL)
  14. washthe combined ether extracts were washed with brine (1×50 mL)
  15. filtrationfiltered through 1PS filter paper
  16. customThe ether was evaporated
  17. distillationthe residue was distilled

Sources & evidence

ORD record
ord-a0c72616c4e74eef87b7f69d53118e54
Source dataset
uspto-grants-1997_10
Patent number
US05675038

Reaction notes

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