Cetyl Alcohol → Hexadecyl phosphorodichloridate

HRID 248160Notes

Reaction equation

HRID 248160 reaction equation
[P:1]([Cl:5])(Cl)([Cl:3])=[O:2].[CH2:6]([OH:22])[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][CH2:20][CH3:21]>C(Cl)(Cl)(Cl)Cl>[P:1]([Cl:5])([Cl:3])(=[O:2])[O:22][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][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 2682Cetyl AlcoholHCID 24813Phosphorus oxychloride

Product 1

HCID 21666871Hexadecyl phosphorodichloridate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a moisture protected solution of 28.4 ml of phosphorous oxychloride in 200 ml of carbon tetrachloride is added dropwise with stirring a solution of 50 g of 1-hexadecanol in 125 ml of carbon tetrachloride. After stirring at ambient temperature for 18 hours, the solvent is removed and the residue evaporated with toluene several times to give 71 g of the desired product as a vacuum dried water white oil.

Workup

  1. customthe solvent is removed
  2. customthe residue evaporated with toluene several times

Sources & evidence

ORD record
ord-1b159444d1244d48bc290c258391c5e9
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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