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Water → 9-Octadecynamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-

HRID 371377
Notes
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Reaction equation

HRID 371377 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][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].O>CN(C)C=O.CCOCC>[CH2:7]([NH:8][C:15](=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[C:24][CH2:25][CH2:26][CH2:27][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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 8212Stearoyl chlorideHCID 14798Sodium HydroxideHCID 165576Phenol, 4-(aminomethyl)-2-methoxy-, hydrochloride (1:1)

Product 1

HCID 30245869-Octadecynamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 6228DimethylformamideSolvent2×

Procedure

2.4 g of 4-hydroxy-3-methoxybenzylamine-HCl was suspended in 35 ml of N,N-dimethylformamide (DMF), and stirred. Added were 5 ml of a 5N solution of NaOH, and the mixture was stirred for an additional 10 to 15 minutes. The DMF mixture was chilled in an ice bath, and the stearoyl chloride, prepared above and dissolved in ether, was added dropwise. The mixture was then stirred for 3 hours, allowing it to come to room temperature. The mixture was then poured into 300 ml water, layers separated, and the aqueous layer extracted with ethyl ether. The extracts were washed with HCl, sodium bicarbonate, water, and brine, and then dried and filtered. 5.3 g of crude N-vanillyl-9-octadecynamide was obtained. Purification by recrystallization from toluene and hexane, and then benzene and hexane, gave 2.8 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 an additional 10 to 15 minutes
  3. additionwas added dropwise
  4. stirringThe mixture was then stirred for 3 hours
  5. customto come to room temperature
  6. customseparated
  7. extractionthe aqueous layer extracted with ethyl ether
  8. washThe extracts were washed with HCl, sodium bicarbonate, water, and brine
  9. customdried
  10. filtrationfiltered

Sources & evidence

ORD record
ord-aa01aae4fdf74e77994208ee264f52ce
Source dataset
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04532139

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes