Hydrochloric Acid → Diphenyl chlorophosphate

HRID 1166406Notes

Reaction equation

HRID 1166406 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[P:8]([Cl:12])(Cl)(Cl)=[O:9].Cl.CN(C)[C:16](=[O:18])[CH3:17]>>[O:7]([P:8]([Cl:12])([O:18][C:16]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:17]=1)=[O:9])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 996Phenol2×HCID 24813Phosphorus oxychloride2×HCID 31374Dimethylacetamide

Product 1

HCID 75654Diphenyl chlorophosphate

Conditions

Temperature
70 °C

Procedure

To a one liter four-inlet flask equipped with a temperature controller, a reflux condenser, a nitrogen feed and a mechanical stirrer, 2 moles (188 g) phenol and 500 ml N,N-dimethyl acetamide (DMAc) were added. The mixture was heated to 70° C. and then stirred. The mixture was heated to a temperature of 90° C. and the stirring was continued until phenol was dissolved completely. To this solution was added slowly 1.5 mole (230 g) phosphoryl chloride (POCl3) within two hours. The evolution of HCl gas was detected immediately. The temperature was increased to 135-138° C. and maintained at the reflux temperature for 12 hours after the addition of POCl3 was completed. HCl evolution subsided. The mixture was then cooled to room temperature and purified with dichloromethane to yield liquid diphenoxy phosphoryl chloride [DPOC; (II′)]. Yield, 96%. Anal. Calcd. for C12H10PO3Cl: C, 53.53; H, 3.72; O, 17.84; P, 11.52; Cl, 13.28. Found: C, 53.49; H, 3.70; O, 17.64; P, 11.64; Cl, 13.53. EIMS, m/z: 251 (90. M+).

Workup

  1. customTo a one liter four-inlet flask equipped with a temperature controller, a reflux condenser
  2. temperatureThe mixture was heated to a temperature of 90° C.
  3. dissolutionwas dissolved completely
  4. temperatureThe temperature was increased to 135-138° C.
  5. temperaturemaintained at the reflux temperature for 12 hours
  6. temperatureThe mixture was then cooled to room temperature
  7. custompurified with dichloromethane

Sources & evidence

ORD record
ord-877fca4862804523acab2f8b8a695b0f
Source dataset
uspto-grants-2003_09
Patent number
US06613848B1

Reaction notes

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