Sodium Hydroxide → 9,12-Octadecadienamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-, (E,E)-

HRID 463750

Reaction equation

HRID 463750 reaction equation
Cl.[OH:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][C:4]=1[O:11][CH3:12].[OH-].[Na+].[C:15](Cl)(=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]/[CH2:25]/[CH:26]=[CH:27]/[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>O1CCCC1>[CH2:7]([NH:8][C:15](=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]/[CH2:25]/[CH:26]=[CH:27]/[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:6]1[CH:9]=[CH:10][C:3]([OH:2])=[C:4]([O:11][CH3:12])[CH:5]=1.[C:15]([NH2:8])(=[O:33])[CH:16]=[CH:17][CH:18]=[CH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 165576Phenol, 4-(aminomethyl)-2-methoxy-, hydrochloride (1:1)HCID 53655789,12-Octadecadienoyl chloride, (9Z,12Z)-

Product 2

HCID 65071499,12-Octadecadienamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-, (E,E)-HCID 54225156Octadecadienamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-vanillyl-(E,E)-9,12-octadecadienamide was synthesized by the following method: ##STR5## Specifically 6.88 g of 4-hydroxy-3-methoxybenzylamine-HCl was dissolved in 50 ml of tetrahydrofuran (THF), and stirred. Added were 14 ml of a 5N solution of NaOH, and the mixture was stirred for 10 to 15 minutes. Then 10.6 g of (E,E)-9,12 octadecadienoyl chloride (linoelaidoyl chloride), dissolved in THF, was added dropwise. The mixture was then stirred overnight, allowing it to come to room temperature. The solvent was evaporated and the residue partitioned between ethyl ether and water. The organic phase extract was washed with HCl, sodium bicarbonate, water, and brine, and then dried and filtered. 16 g of crude N-vanillyl-(E,E)-9,12)-octadecadienamide was obtained. Purification by recrystallization from ether and pentane gave 9.4 g of analytically pure product. Its structure was confirmed via nuclear magnetic resonance and infrared spectroscopy.

Workup

  1. additionAdded
  2. stirringthe mixture was stirred for 10 to 15 minutes
  3. additionwas added dropwise
  4. stirringThe mixture was then stirred overnight
  5. customto come to room temperature
  6. customThe solvent was evaporated
  7. customthe residue partitioned between ethyl ether and water
  8. extractionThe organic phase extract
  9. washwas washed with HCl, sodium bicarbonate, water, and brine
  10. customdried
  11. filtrationfiltered

Sources & evidence

ORD record
ord-7ab17574bcec434eb7d00cc8a086cd2e
Source dataset
uspto-grants-1985_10
Patent number
US04544669

Linked notes

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