O-Xylene → RU78783

HRID 1380015

Reaction equation

HRID 1380015 reaction equation
[Na].[C:2]1([CH3:9])[C:3](C)=[CH:4][CH:5]=[CH:6][CH:7]=1.[P:10]([O-:17])([O:14]CC)[O:11]CC.C(Cl)(Cl)C1C=CC=CC=1>O1CCCC1>[C:2]1([CH:9]([P:10]([OH:17])(=[O:11])[OH:14])[P:10]([OH:17])(=[O:14])[OH:11])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 7411Benzal chlorideHCID 3780918DiethylphosphiteHCID 5360545Sodium2×

Product 1

HCID 447537RU78783

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
62 °C

Procedure

There were charged into the reaction vessel 23.0 grams (1.0 mole) of sodium metal along with 90 cc. of xylene and 80 cc. of tetrahydrofurane. The vessel was placed under a nitrogen blanket and 138.10 grams (1.0 mole) of diethyl phosphite added over a 35 minute period. An exothermic reaction ensued which was maintained at 62° C. by external cooling. After addition was complete the mixture was heated to 100° C. and held there until all of the sodium metal was gone. The mixture was cooled to 60° to 70° C. and 80.50 grams (0.5 ,ole) of benzal chloride were added gradually over a 25 minute period. An exothermic reaction ensued which was maintained at 60° to 70° C. by external cooling. The mixture was then heated for 4 hours at 70° to 75° C., cooled to 60° C. The liquid material was separated from the solid and the solid boiled 8 times with 100 cc. of benzene to extract the organic material. The eluate product was then distilled, terminal conditions being a pot temperature of 201° C., distillate temperature 125° C. and pressure 6 mm. The solid residue of 70 grams was tetraethyl phenyl methane diphosphonate. This product was hydrolyzed and the hydrolysis product purifid as in Example 1 to obtain phenyl methane diphosphonic acid.

Workup

  1. additionadded over a 35 minute period
  2. customAn exothermic reaction
  3. additionAfter addition
  4. temperaturewas heated to 100° C.
  5. temperatureThe mixture was cooled to 60° to 70° C.
  6. customAn exothermic reaction
  7. temperaturewas maintained at 60° to 70° C. by external cooling
  8. temperatureThe mixture was then heated for 4 hours at 70° to 75° C.
  9. temperaturecooled to 60° C
  10. customThe liquid material was separated from the solid
  11. extractionof benzene to extract the organic material
  12. distillationThe eluate product was then distilled
  13. customa pot temperature of 201° C., distillate temperature 125° C. and pressure 6 mm

Sources & evidence

ORD record
ord-d394fb67cabd4032aa1d696a59a6b9ab
Source dataset
uspto-grants-1986_04
Patent number
US04579720

Linked notes

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