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

HRID 1022392Notes

Reaction equation

HRID 1022392 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[Cl-].[Mg+2].[Cl-].[P:13]([Cl:17])(Cl)(Cl)=[O:14]>O>[C:3]1([O:9][P:13]([Cl:17])(=[O:14])[O:9][C:3]2[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 113352,6-DimethylphenolHCID 24813Phosphorus oxychlorideHCID 5360315Magnesium Chloride

Product 1

HCID 9923313Bis(2,6-dimethylphenyl) Chlorophosphate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A 1,000-ml four-necked flask provided with a stirring machine, a thermometer, a dropping funnel, and a nitrogen-introducing pipe was mounted with a condenser to which a water scrubber had been connected, and then 2.0 mol (244 g) of 2,6-dimethylphenol, and 0.016 mol (1.5 g) of magnesium chloride were loaded into the resultant reactor. The atmosphere in the reactor was replaced with nitrogen and then its temperature was increased to 120° C. 1.0 Mole (153 g) of phosphorus oxychloride was dropped into the reactor at that temperature over 2 hours. After the completion of the dropping, the temperature was increased to 180° C. over 2 hours. Thus, di(2,6-xylyl)phosphorochloridate was obtained. The temperature in the flask was cooled to 20° C., and then 0.5 mol (55 g) of 1,3-benzenediol and 0.016 mol (1.5 g) of magnesium chloride were loaded into the flask. The temperature was increased to 180° C. over 2 hours and then the mixture was aged for 2 hours. After that, the catalyst was removed by an ordinary method and then the remainder was dried at 140° C. under reduced pressure. Thus, X-1 represented by the following general formula (5) was obtained.

Workup

  1. customA 1,000-ml four-necked flask provided with a stirring machine
  2. additiona thermometer, a dropping funnel, and a nitrogen-introducing pipe
  3. customwas mounted with a condenser to which
  4. temperatureAfter the completion of the dropping, the temperature was increased to 180° C. over 2 hours

Sources & evidence

ORD record
ord-7c9ac8cc6dcb41f590face4d10fe0590
Source dataset
uspto-grants-2014_05
Patent number
US08722596B2

Reaction notes

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