Ethanol → 4-Hexadecylaminocinnamic acid

HRID 1702673Notes

Reaction equation

HRID 1702673 reaction equation
[CH2:1]([NH:17][C:18]1[CH:30]=[CH:29][C:21]([CH:22]=[CH:23][C:24]([O:26]CC)=[O:25])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[OH-].[Na+].O.C(O)C>C(O)(=O)C>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([CH:22]=[CH:23][C:24]([OH:26])=[O:25])=[CH:29][CH:30]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 53709874Ethyl 4-hexadecylaminocinnamate

Product 1

HCID 539289584-Hexadecylaminocinnamic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl p-aminocinnamate, one equivalent of 1-bromohexadecene, one equivalent of anhydrous potassium carbonate in hexamethylphosphoramide is heated for 20 hours at 60° C. The mixture is then cooled, diluted with water and extracted with ether. The combined ether extracts are dried, filtered and evaporated to provide ethyl 4-hexadecylaminocinnamate. The ester is hydrolyzed with sodium hydroxide in a 1:1 water:ethanol solution at steam bath temperature for 10 hours. The hot solution is then acidified with acetic acid, cooled, filtered and the precipitate is washed with water. Recrystallization from chloroform yields 4-hexadecylaminocinnamic acid.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washthe precipitate is washed with water
  4. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-cbe28f74cedc4a3389bd7a88176c0579
Source dataset
uspto-grants-1982_09
Patent number
US04348399

Reaction notes

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