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Pentaerythritol → Pentaerythritol, cyclic phosphate (1:1) (8CI)

HRID 2254867
Notes
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Reaction equation

HRID 2254867 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[P:10](Cl)(Cl)(Cl)=[O:11]>CC(C1C=CC(OP(OC2C=CC=CC=2)(OC2C=CC=CC=2)=O)=CC=1)C.CC(C1C=CC=C(OP(OC2C=CC=CC=2)(OC2C=CC=CC=2)=O)C=1)C.CC(C1C(OP(OC2C=CC=CC=2)(OC2C=CC=CC=2)=O)=CC=CC=1)C>[CH2:4]1[O:5][P:10]2([O:7][CH2:6][C:3]1([CH2:8][OH:9])[CH2:2][O:1]2)=[O:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 8285PentaerythritolHCID 24813Phosphorus oxychloride

Product 1

HCID 199942Pentaerythritol, cyclic phosphate (1:1) (8CI)Yield 75%

Reagents, catalysts & solvents 1

HCID 24832072HCID 24832072, compoundSolvent

Conditions

Temperature
100 °C

Procedure

In a 250 mL four-necked reaction flask fitted with a mechanical stirrer, pot thermometer, addition funnel, and condenser with gas outlet were placed 42.5 g (0.313 mole) of pentaerythritol and 150 mL of PHOSFLEX 41P brand of isopropylated triphenyl phosphate under nitrogen. The mixture was stirred and heated at 95° C. as 49.2 g (0.321 mole) of phosphorus oxychloride was added dropwise over five hours. The resulting white slurry was heated to 100° C. with a nitrogen gas sparge for eight hours to remove HCl. The mixture was cooled to 50° C. and filtered. The solid was washed three times with 40 mL of hexane and dried at 100° C./2 mm Hg for sixteen hours to give 42.3 g (71.2% yield) of crude pentaerythritol phosphate alcohol (2,6,7-trioxa- 1-phosphabicyclo [2.2.2]octane-4-methanol-1-oxide). The product had a 31P NMR resonance at -6.0 ppm in d6 -DMSO.

Workup

  1. customIn a 250 mL four-necked reaction flask fitted with a mechanical stirrer
  2. additionpot thermometer, addition funnel, and condenser with gas outlet
  3. additionwas added dropwise over five hours
  4. customsparge for eight hours
  5. customto remove HCl
  6. temperatureThe mixture was cooled to 50° C.
  7. filtrationfiltered
  8. washThe solid was washed three times with 40 mL of hexane
  9. customdried at 100° C./2 mm Hg for sixteen hours

Sources & evidence

ORD record
ord-519b9d3dc15c4773ba4cc02668f28e1f
Source dataset
uspto-grants-1993_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05237085

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes