Cetyl Alcohol → Hexadecyl acrylate

HRID 1857343Notes

Reaction equation

HRID 1857343 reaction equation
[CH2:1]([OH:17])[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].[C:18](Cl)(=[O:21])[CH:19]=[CH2:20]>C1C=CC=CC=1>[CH2:1]([O:17][C:18](=[O:21])[CH:19]=[CH2:20])[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

4

Reactant 2

HCID 2682Cetyl AlcoholHCID 13140Acryloyl chloride

Product 1

HCID 83410Hexadecyl acrylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

Hexadecanylacrylate was prepared by dissolving 10 g of hexadecanol in 50 ml of benzene. A 1.2 molar excess of acryloylchloride was added to the mixture and refluxed at 80° C. for 24 hours with stirring. The reaction mixture was allowed to cool to room temperature and the solvent was removed by roto-evaporation and room temperature water bath. The product was redissolved and 100 ml of diethyl ether and extracted five times with an equal volume of 10% NaHCO3 in a separatory funnel. The ether fraction was isolated and the solvent was removed by roto-evaporation at room temperature followed by vacuum drying in a room temperature oven. Hexadecanylacrylate is represented by the formula (XI): ##STR13##

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent was removed by roto-evaporation and room temperature water bath
  3. dissolutionThe product was redissolved
  4. extraction100 ml of diethyl ether and extracted five times with an equal volume of 10% NaHCO3 in a separatory funnel
  5. customThe ether fraction was isolated
  6. customthe solvent was removed by roto-evaporation at room temperature
  7. customdrying in a room temperature oven

Sources & evidence

ORD record
ord-1c6c122d5d6747a5a027ffb2af3f2d11
Source dataset
uspto-grants-2000_11
Patent number
US06147068

Reaction notes

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