Toluene → HCID 19090311, compound

HRID 1589943Notes

Reaction equation

HRID 1589943 reaction equation
[CH:1]([P:11]([O:16][CH2:17][CH3:18])(=[O:15])[O:12][CH2:13][CH3:14])([P:3]([O:8][CH2:9][CH3:10])(=[O:7])[O:4][CH2:5][CH3:6])[CH3:2].[CH:19]([CH:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=C.[H-].[Na+].[H][H].[C:33]1(C)C=CC=CC=1>>[CH:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:2][C:1]([P:3]([O:4][CH2:5][CH3:6])(=[O:7])[O:8][CH2:9][CH3:10])([P:11]([O:16][CH2:17][CH3:18])(=[O:15])[O:12][CH2:13][CH3:14])[CH3:33])=[CH2:19]

Participants

6

Reactant 5

HCID 1140TolueneHCID 24758Sodium hydrideHCID 11077490P,P,P′,P′-Tetraethyl P,P′-ethylidenebis[phosphonate]2×HCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-2×HCID 178418361HCID 178418361, compound

Product 1

HCID 19090311HCID 19090311, compoundYield 81%

Procedure

Tetraethyl 1-(vinylphenyl)propane-2,2-bisphosphonate (4) was prepared from compound (3) and vinylbenzyl chloride, of which 70% was in meta- and 30% in para-form, in the following manner. In a flame dried two-necked flask equipped with a dropping funnel and protected with nitrogen gas 100 ml of dry toluene and 2.69 g (0.112 moles) of dry sodium hydride were introduced. Mixing was started and 30.0 g (0.099 moles) of compound (3) was dropped to the mixture. When the addition was complete and the release of hydrogen had ceased, stirring was continued for an additional hour at room temperature. Thereafter 18.3 g (0.12 moles) of vinylbenzyl chloride was dropped to the mixture, and stirring was continued under the protective gas at room temperature until the reaction was complete. This lasted from one to two weeks. The reaction mixture was concentrated on a rotary vacuum evaporator. The residue was dissolved in diethyl ether, washed three times with water, dried over sodium sulphate and the solvent evaporated in vacuum. 33.5 g (81%) of the raw product (4) was obtained, of which about 80% was compound (4) and 20% vinylbenzyl chloride. The raw product was used unpurified in the subsequent reaction.

Workup

  1. customIn a flame dried two-necked flask equipped with a dropping funnel
  2. additionwere introduced
  3. additionMixing
  4. additionWhen the addition
  5. waitwas continued for an additional hour at room temperature
  6. stirringstirring
  7. customwas continued under the protective gas at room temperature until the reaction
  8. waitThis lasted from one to two weeks
  9. concentrationThe reaction mixture was concentrated on a rotary vacuum evaporator
  10. dissolutionThe residue was dissolved in diethyl ether
  11. washwashed three times with water
  12. dry with materialdried over sodium sulphate
  13. customthe solvent evaporated in vacuum

Sources & evidence

ORD record
ord-4663203ce9e54d1e8c2ffcae257470d2
Source dataset
uspto-grants-1993_04
Patent number
US05200554

Reaction notes

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