Benzene → 3,7,11,15-Tetramethylhexadecyl 2-trimethylammonioethyl phosphate

HRID 2107808Notes

Reaction equation

HRID 2107808 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][CH:7]([CH2:9][CH2:10][CH2:11][CH:12]([CH2:14][CH2:15][CH2:16][CH:17]([CH2:19][CH2:20][OH:21])[CH3:18])[CH3:13])[CH3:8])[CH3:3].[P:22](Cl)(Cl)(=[O:27])[O:23][CH2:24][CH2:25]Br.[N:30]1[CH:35]=CC=C[CH:31]=1.[OH2:36].[CH:37]1C=CC=CC=1>>[P:22]([O-:27])([O:23][CH2:24][CH2:25][N+:30]([CH3:35])([CH3:37])[CH3:31])([O:21][CH2:20][CH2:19][CH:17]([CH3:18])[CH2:16][CH2:15][CH2:14][CH:12]([CH3:13])[CH2:11][CH2:10][CH2:9][CH:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])=[O:36]

Participants

6

Reactant 5

HCID 241BenzeneHCID 962WaterHCID 1049PyridineHCID 102459DihydrophytolHCID 4684632(2-Bromoethoxy)phosphonoyl dichloride

Product 1

HCID 148562013,7,11,15-Tetramethylhexadecyl 2-trimethylammonioethyl phosphateYield 43%

Procedure

Dihydrophytol (0.60 g) and bromoethyl phosphorodichloridate (0.83 g) were dissolved in dry benzene (10 ml). To the solution was added dropwise dry pyridine (0.2 ml) under stirring. The mixture was stirred at room temperature for three hours, then cooled with ice, to which was added 2 ml of water. The mixture was again stirred vigorously at room temperature for two hours. The solvent was evaporated off, and the residue was dissolved in ether. The ether solution was washed with water, and then concentrated to dryness. The residue was dissolved in toluene (10 ml) containing trimethylamine (2 g), and the solution was left standing for five days. The reaction solution was concentrated under reduced pressure. The residue was subjected to a silica-gel chromatography (eluent, methanol) to yield 0.404 g (43%) of the object compound as colorless solid matter.

Workup

  1. stirringThe mixture was stirred at room temperature for three hours
  2. temperaturecooled with ice, to which
  3. stirringThe mixture was again stirred vigorously at room temperature for two hours
  4. customThe solvent was evaporated off
  5. dissolutionthe residue was dissolved in ether
  6. washThe ether solution was washed with water
  7. concentrationconcentrated to dryness
  8. dissolutionThe residue was dissolved in toluene (10 ml)
  9. additioncontaining trimethylamine (2 g)
  10. waitthe solution was left
  11. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e39d53309b7341749649bf1efa31e2ce
Source dataset
uspto-grants-1990_06
Patent number
US04935520

Reaction notes

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