Water → HCID 53745224, compound

HRID 247719Notes

Reaction equation

HRID 247719 reaction equation
[CH2:1]([OH:21])[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][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[CH3:22][O:23][C:24]1[CH:38]=[CH:37][CH:36]=[CH:35][C:25]=1[C:26]([O:33][CH3:34])=[C:27]([O:31][CH3:32])[C:28](Cl)=[O:29].O=P(Cl)(Cl)Cl.O>N1C=CC=CC=1>[CH3:22][O:23][C:24]1[CH:38]=[CH:37][CH:36]=[CH:35][C:25]=1[C:26]([O:33][CH3:34])=[C:27]([O:31][CH3:32])[C:28]([O:21][CH2:1][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][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 124041-EicosanolHCID 24813Phosphorus oxychlorideHCID 54502213HCID 54502213, compound

Product 1

HCID 53745224HCID 53745224, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.9 g of 1-eicosanol dissolved in 50 ml of anhydrous pyridine are placed in a 100 ml flask equipped with a stirrer, a thermometer and a dehydrating valve. To this solution there are added 2.5 g of trimethoxycinnamoyl chloride and 0.01 ml of POCl3. The reaction mixture is left alone at room temperature overnight and is then poured into 200 ml of water. After filtration, the precipitate formed is crystallized from 30 ml of methanol. After drying, 4.2 g of eicosyl trimethoxycinnamate having the following characteristics are obtained:

Workup

  1. customare placed in a 100 ml flask
  2. customequipped with a stirrer
  3. filtrationAfter filtration
  4. customthe precipitate formed
  5. customis crystallized from 30 ml of methanol
  6. customAfter drying

Sources & evidence

ORD record
ord-c0cf6a08059e4f808c917fbfe26057e8
Source dataset
uspto-grants-1987_11
Patent number
US04709076

Reaction notes

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