2,4-Dichlorophenol → Bis(2,4-dichlorophenyl) phosphorochloridate

HRID 330058Notes

Reaction equation

HRID 330058 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[P:10]([Cl:14])(Cl)(Cl)=[O:11]>>[P:10]([Cl:14])(=[O:11])([O:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])[O:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

Participants

3

Reactant 2

HCID 84492,4-Dichlorophenol2×HCID 24813Phosphorus oxychloride2×

Product 1

HCID 5012072Bis(2,4-dichlorophenyl) phosphorochloridate

Procedure

The title compound was prepared by the general method of Example 1 with the following modifications. (1) The molar ratio of 2,4-dichlorophenol to phosphorus oxychloride was increased from 1.33 to 1.85 by using 189.99 g (1.165 mole) of 2,4-dichlorophenol and 96.60 g (0.63 mole) of phosphorus oxychloride. (2) The reaction time at 120° was increased to about 24 hours. (3) The product was crystallized using a larger quantity of hexane (570 ml, or 3 ml per gram of starting 2,4-dichlorophenol) at -15°. Analysis by GLPC indicated 82% purity (by weight) of bis(2,4-dichlorophenyl) phosphorochloridate, with contamination by a trace of 2,4-dichlorophenyl phosphorodichloridate and 18% (by weight) of tris(2,4-dichlorophenyl) phosphate. The yield of the bis(2,4-dichlorophenyl) phosphorochloridate when corrected for purity was 125 g (53%)

Workup

  1. custom(3) The product was crystallized
  2. customat -15°

Sources & evidence

ORD record
ord-9b0fc3cb7f1e4fc09bcd4d25a7bdbd8c
Source dataset
uspto-grants-1990_01
Patent number
US04894450

Reaction notes

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