2,6-Dimethylphenol → Bis(2,6-dimethylphenyl) Chlorophosphate

HRID 333663Notes

Reaction equation

HRID 333663 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[Cl-].[Cl-].[Cl-].[Al+3].[P:14]([Cl:18])(Cl)(Cl)=[O:15]>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][P:14]([Cl:18])(=[O:15])[O:9][C:3]1[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

4

Reactant 3

HCID 113352,6-DimethylphenolHCID 24813Phosphorus oxychlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 9923313Bis(2,6-dimethylphenyl) Chlorophosphate

Procedure

2,6-dimethylphenol (1 g, 8.18 mmol) and aluminum trichloride (109 mg, 0.818 mmol, 0.1 eq) were added to a microwave vial. Phosphorus oxychloride (0.375 mL, 4.09 mmol, 0.5 eq) was added, the vial was sealed and subsequently heated in the microwave for 1 h. Reaction progress was monitored by TLC, and the reaction was quenched before going to completion. The reaction mixture was diluted with dicholoromethane, washed with water and brine, dried over MgSO4, and filtered through celite. The filtrate was concentrated under reduced pressure providing an oily residue that was taken directly to the next step without further purification.

Workup

  1. customthe vial was sealed
  2. temperaturesubsequently heated in the microwave for 1 h
  3. customReaction progress
  4. customthe reaction was quenched
  5. additionThe reaction mixture was diluted with dicholoromethane
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered through celite
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customproviding an oily residue that
  11. customwas taken directly to the next step without further purification

Sources & evidence

ORD record
ord-4cd79835278c4c3a8d99ad5bb7718cba
Source dataset
uspto-grants-2014_11
Patent number
US08883765B2

Reaction notes

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