1-Bromohexadecane → Hexadecyl(triphenyl)phosphanium bromide

HRID 634611Notes

Reaction equation

HRID 634611 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([Br:36])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>>[Br-:36].[CH2:35]([P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20]

Participants

3

Reactant 2

HCID 82131-BromohexadecaneHCID 11776Triphenylphosphine

Product 1

HCID 3084210Hexadecyl(triphenyl)phosphanium bromideYield 45.7%

Conditions

Temperature
180 °C

Procedure

In a 100 ml flask equipped with a stirrer, a condenser and a calcium chloride dryer tube were charged 8.6 g of triphenylphosphine and 10 g of n-hexadecyl bromide, and under nitrogen atmosphere, the mixture was heated at 180° C. for 10 hours on an oil bath. After cooling the reaction mixture to room temperature, precipitated solid material was pulverized in acetone and collected by filtration under reduced pressure. The resulting crystals were washed with acetone to obtain 8.5 g of the title compound. Melting point: 128° C.

Workup

  1. customIn a 100 ml flask equipped with a stirrer, a condenser and a calcium chloride dryer tube
  2. temperatureAfter cooling the reaction mixture to room temperature
  3. customprecipitated solid material
  4. filtrationcollected by filtration under reduced pressure
  5. washThe resulting crystals were washed with acetone

Sources & evidence

ORD record
ord-ef9b1a08a9874b4c920fd9f3857f4664
Source dataset
uspto-grants-2001_02
Patent number
US06184180B2

Reaction notes

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