Water → HCID 178527067, compound

HRID 1618357Notes

Reaction equation

HRID 1618357 reaction equation
[H-].[Na+].[CH2:3](P(=O)(OCC)OCC)[P:4](=[O:11])([O:8]CC)[O:5]CC.O>CC1C=CC=CC=1>[PH:4](=[O:5])([O-:11])[O-:8].[C+4:3].[C+4:3].[C+4:3].[C+4:3].[C+4:3].[C+4:3].[C+4:3].[C+4:3].[C+4:3].[C+4:3].[C+4:3].[C+4:3].[C+4:3].[C+4:3].[C+4:3].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8].[PH:4](=[O:5])([O-:11])[O-:8]

Participants

5

Reactant 3

HCID 962WaterHCID 15455Tetraethyl methylenediphosphonateHCID 24758Sodium hydride

Product 1

HCID 178527067HCID 178527067, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
12.5 °C

Procedure

1.1 g (0.0275 mol) sodium hydride (60% content) is added to a 100 ml three-necked bottle under the protection of nitrogen, paraffin oil is removed by rinsing twice with 10 ml n-hexane each time; then, 10 ml methylbenzene is added, 8.6 g tetraethyl methylenediphosphonate (0.03 mol) is dropwise added to the solution of 20 ml methylbenzene under magnetic stirring, the temperature of cold water bath is maintained within a range from 10 to 15° C. while addition, a large amount of gas is discharged, the addition can be finished about half an hour later, and stirring is continued for reaction for half an hour; afterwards, 5.1 g C-14 aldehyde (3B) (prepared in the embodiment 2, 0.025 mol) is dropwise added and dissolved in the solution of 20 ml methylbenzene, the temperature of cold water bath is maintained within a range from 10 to 15° C. while addition, the addition can be finished about half an hour later, and stirring is continued for reaction for half an hour. 20 ml water is added to the reaction mixture solution, which is followed by stirring for 10 minutes and layering, organic layer is rinsed by 20 ml sodium hydride aqueous solution with the concentration of 10%, dried by magnesium sulfate and filtered, and the solvent is dried by evaporation under reduced pressure to obtain 7.5 g 1,3,6,10-tetra-double bond pentadec-carbon phosphonate (4) crude product, which is light brown liquid and has the gas phase content of 93.2% and the yield of 88.5%.

Workup

  1. customis removed
  2. washby rinsing twice with 10 ml n-hexane each time
  3. additionthen, 10 ml methylbenzene is added
  4. additionthe addition
  5. waitcan be finished about half an hour
  6. customis continued for reaction for half an hour
  7. additionis dropwise added
  8. temperaturethe temperature of cold water bath is maintained within a range from 10 to 15° C. while addition
  9. additionthe addition
  10. waitcan be finished about half an hour
  11. stirringlater, and stirring
  12. customis continued for reaction for half an hour
  13. stirringby stirring for 10 minutes
  14. washlayering, organic layer is rinsed by 20 ml sodium hydride aqueous solution with the concentration of 10%
  15. dry with materialdried by magnesium sulfate
  16. filtrationfiltered
  17. customthe solvent is dried by evaporation under reduced pressure

Sources & evidence

ORD record
ord-aa3db4b69647464b93a36cef22f184ad
Source dataset
uspto-grants-2014_07
Patent number
US08765988B2

Reaction notes

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