4-Isopropylphenol → Bis[4-(propan-2-yl)phenyl] phosphorochloridate

HRID 2057685Notes

Reaction equation

HRID 2057685 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[P:11]([Cl:15])(Cl)(Cl)=[O:12].[Cl-].[NH4+]>>[P:11]([Cl:15])(=[O:12])([O:10][C:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1)[O:10][C:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 74654-Isopropylphenol2×HCID 24813Phosphorus oxychlorideHCID 25517Ammonium Chloride

Product 1

HCID 3085707Bis[4-(propan-2-yl)phenyl] phosphorochloridate

Conditions

Temperature
135 °C

Procedure

Following the procedure of U.S. Patent No. 3,773,866, 54.0 g (0.4 mole) of 4-isopropylphenol was added to 73.4 g (0.47 moles) of phosphorus oxychloride and 0.6 g of ammonium chloride at 105° C. over a 1.5 hour period. After heating an additional 1.5 hour the temperature was raised to 135° C. and a second 54 g portion of 4-isopropylphenol was added. The mixture was stirred at 168° C. overnight, and purified by fractional distillation. The fraction which distilled at 258° C. (0.5 torr) was identified as 97% pure by glc.

Workup

  1. temperatureAfter heating an additional 1.5 hour the temperature
  2. distillationpurified by fractional distillation
  3. distillationThe fraction which distilled at 258° C. (0.5 torr)

Sources & evidence

ORD record
ord-cef544b08bc14e189aef5e910214c7ae
Source dataset
uspto-grants-1980_07
Patent number
US04212757

Reaction notes

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