4-Coumaric acid → Hexadecyl 3-(4-hydroxyphenyl)prop-2-enoate

HRID 896724Notes

Reaction equation

HRID 896724 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH2:13](O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[CH2:28]([O:9][C:8](=[O:10])[CH:7]=[CH:6][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:12][CH:11]=1)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13]

Participants

6

Reactant 4

HCID 3224-Coumaric acidHCID 1140TolueneHCID 2682Cetyl AlcoholHCID 6101p-Toluenesulfonic acid

Product 1

HCID 54379095Hexadecyl 3-(4-hydroxyphenyl)prop-2-enoateYield 21.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Hydroxy cinnamic acid (10 g, 61 mmol) was combined with 1-hexadecanol (14.0 g, 58 mmol), p-toluenesulfonic acid (1.2 g, 6.3 mmol) and 100 ml toluene and heated to 140° C. for 24 h with continual removal of water using a Dean-Stark distillation apparatus. The mixture was cooled to room temperature and 50 ml ethyl acetate added. The solution was washed with water, 5% sodium hydrogen carbonate, brine and then dried over magnesium sulfate. The product was recrystallized from ethyl acetate to give 4.8 g 3-(4-hydroxy-phenyl)-acrylic acid hexadecyl ester.

Workup

  1. distillationa Dean-Stark distillation apparatus
  2. addition50 ml ethyl acetate added
  3. washThe solution was washed with water, 5% sodium hydrogen carbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. customThe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c67a929284f64ecaa94266ffdd20d7f4
Source dataset
uspto-grants-2005_07
Patent number
US06919404B2

Reaction notes

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