4-tert-Butylphenol → 4-tert-Butylphenyl phosphorodichloridate

HRID 1658650Notes

Reaction equation

HRID 1658650 reaction equation
[P:1]([Cl:5])(Cl)([Cl:3])=[O:2].[C:6]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7]>N1C=CC=CC=1>[P:1]([Cl:5])([Cl:3])(=[O:2])[O:16][C:13]1[CH:14]=[CH:15][C:10]([C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 73934-tert-ButylphenolHCID 24813Phosphorus oxychloride

Product 1

HCID 30847124-tert-Butylphenyl phosphorodichloridateYield 94.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 225 g. phosphoryl chloride and 1.6 g. pyridine there is added 150 g. p-tert-butylphenol over a period of two hours at a temperature of 100°C. The temperature is then raised to 110°C. and held for two hours, stripped and cooled. Distillation of the reaction mixture affords 94.3 percent p-tert-butylphenyl phosphorodichloridate and 2.5 percent di-p-tert-butylphenyl phosphorochloridate.

Workup

  1. additionTo a mixture of 225 g
  2. temperaturecooled
  3. distillationDistillation of the reaction mixture

Sources & evidence

ORD record
ord-a68647a209cb472dbe3cb803b28bb78a
Source dataset
uspto-grants-1976_06
Patent number
US03965220

Reaction notes

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