Monobenzone → HCID 101742540, compound

HRID 2289828Notes

Reaction equation

HRID 2289828 reaction equation
Cl[P:2]1(Cl)[N:7]=[P:6](Cl)(Cl)[N:5]=[P:4](Cl)(Cl)[N:3]=1.[H-].[Na+].[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H][H]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.CO>[CH2:15]([O:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][P:2]2([O:29][C:26]3[CH:25]=[CH:24][C:23]([O:22][CH2:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:28][CH:27]=3)[N:7]=[P:6]([O:29][C:26]3[CH:25]=[CH:24][C:23]([O:22][CH2:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:28][CH:27]=3)([O:29][C:26]3[CH:25]=[CH:24][C:23]([O:22][CH2:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:28][CH:27]=3)[N:5]=[P:4]([O:29][C:26]3[CH:25]=[CH:24][C:23]([O:22][CH2:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:28][CH:27]=3)([O:29][C:26]3[CH:25]=[CH:24][C:23]([O:22][CH2:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:28][CH:27]=3)[N:3]=2)=[CH:27][CH:28]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 7638MonobenzoneHCID 24758Sodium hydrideHCID 220225HexachlorocyclotriphosphazeneHCID 178418361HCID 178418361, compound

Product 1

HCID 101742540HCID 101742540, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 20.00 g (5.74×10-2 mol) of hexachlorocyclotriphosphazene, 22.99 g (0.57 mol) of NaH 60% oil dispersion, and 1.5 g of tetrabutylammonium bromide in 200 mL of THF is treated with 115.1 g (0.57 mol) of 4-(benzyloxy)phenol in 250 mL of THF. This treatment is performed dropwise, waiting each time for hydrogen evolution. The reaction mixture is successively refluxed for 48 hrs, cooled to room temperature, and ultracentrifuged at 8000 rpm to separate the liquid from the solid. The liquor is evaporated to dryness with a rotovap. The solid brown paste obtained is treated successively with methanol to obtain a white powder which is isolated by filtration, thoroughly washed with water and methanol, and dried. The resulting Hexakis(4-benzyloxyphenoxy)cyclotriphosphazene trimer is purified by multiple crystallizations from 50% THF/CH3OH mixtures.

Workup

  1. temperatureThe reaction mixture is successively refluxed for 48 hrs
  2. customto separate the liquid from the solid
  3. customThe liquor is evaporated to dryness with a rotovap
  4. customThe solid brown paste obtained
  5. customto obtain a white powder which
  6. customis isolated by filtration
  7. washthoroughly washed with water and methanol
  8. customdried
  9. customThe resulting Hexakis(4-benzyloxyphenoxy)cyclotriphosphazene trimer is purified by multiple crystallizations from 50% THF/CH3OH mixtures

Sources & evidence

ORD record
ord-c877a5f667fd41b6aca817b0d4c7df74
Source dataset
uspto-grants-2000_07
Patent number
US06093758

Reaction notes

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