1-Bromohexadecane → 1-Dimethoxyphosphorylhexadecane

HRID 465961Notes

Reaction equation

HRID 465961 reaction equation
[CH2:1](Br)[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].[P:18]([O:23]C)([O:21][CH3:22])[O:19][CH3:20]>>[CH2:1]([P:18](=[O:23])([O:21][CH3:22])[O:19][CH3:20])[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

3

Reactant 2

HCID 82131-BromohexadecaneHCID 8472Trimethyl phosphite

Product 1

HCID 3629041-Dimethoxyphosphorylhexadecane

Conditions

Temperature
116 °C

Procedure

A mixture of n-hexadecyl bromide (4.89 g, 16 mmol) and freshly distilled trimethyl phosphite (2.48 g, 20 mmol) is stirred at 116° C. for 24 hours. The excess trimethyl phosphite is then removed by distillation in vacuo and the residue is stored over phosphorus pentoxide in vacuo for 24 hours. The corresponding dimethyl n-hexadecylphosphonate is isolated from the residue by extracting twice with 10 ml of methanol each time. The two methanol extracts are combined and concentrated in vacuo. The oily colorless residue thus obtained, which still contains n-hexadecyl bromide in addition to the methyl n-hexadecylphosphonate, is further reacted with trimethylsilyl chloride (1.02 g, 9.4 mmol) and sodium iodide (1.4 g, 9.4 mmol) in 4.7 ml of anhydrous acetonitrile. The reaction is carried out with stirring at room temperature and lasts 15 minutes.

Workup

  1. customThe excess trimethyl phosphite is then removed by distillation in vacuo
  2. waitthe residue is stored over phosphorus pentoxide in vacuo for 24 hours

Sources & evidence

ORD record
ord-7e0e6e40c4d54412882ff852794fd237
Source dataset
uspto-grants-1992_10
Patent number
US05155099

Reaction notes

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