Hydrochloric Acid → Diphenylmethylphosphonic acid

HRID 362158Notes

Reaction equation

HRID 362158 reaction equation
Br[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[P:15]([O:22]CC)([O:19]CC)[O:16]CC.BrCC.Cl>O>[CH:2]([P:15](=[O:16])([OH:22])[OH:19])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 31215Triethyl phosphiteHCID 236603Bromodiphenylmethane

Product 1

HCID 195023Diphenylmethylphosphonic acidYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzhydrylphosphonic acid was prepared as follows. 308.93 g (1.25 moles) of bromodiphenylmethane (Aldrich Chemical Company) and 240.93 g (1.45 moles) of triethyl phosphite (Aldrich Chemical Company) were combined under nitrogen, heated carefully and maintained at 160° C. with removal of bromoethane by-product by distillation over a period of 4 hours. 750 ml of concentrated hydrochloric acid (~12 molar) and 250 ml of distilled water was added to the crude product and the mixture was refluxed under nitrogen for two days (approximately 40 hours). The frothy mixure was allowed to cool and then filtered. The resulting solid was then washed with water, to remove the remaining hydrochloric acid, and then with petrol (b.p. 60°-80° C.), to remove hydrocarbon by products, for example 1,1,2,2-tetraphenylethane. The solid was then dried in a vacuum oven at 120° C. 250.06 g (81% yield) was obtained.

Workup

  1. temperatureheated carefully
  2. temperaturethe mixture was refluxed under nitrogen for two days (approximately 40 hours)
  3. temperatureto cool
  4. filtrationfiltered
  5. washThe resulting solid was then washed with water
  6. customto remove the remaining hydrochloric acid
  7. customwith petrol (b.p. 60°-80° C.), to remove hydrocarbon by products
  8. customThe solid was then dried in a vacuum oven at 120° C
  9. custom250.06 g (81% yield) was obtained

Sources & evidence

ORD record
ord-345d7f2ce91a4a449be91fb07170f895
Source dataset
uspto-grants-1999_02
Patent number
US05868959

Reaction notes

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