Water → HCID 178527067, compound

HRID 1618359Notes

Reaction equation

HRID 1618359 reaction equation
[CH2:1](P(=O)(OCC)OCC)[P:2](=[O:9])([O:6]CC)[O:3]CC.O>CCOCC>[PH:2](=[O:3])([O-:9])[O-:6].[C+4:1].[C+4:1].[C+4:1].[C+4:1].[C+4:1].[C+4:1].[C+4:1].[C+4:1].[C+4:1].[C+4:1].[C+4:1].[C+4:1].[C+4:1].[C+4:1].[C+4:1].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6].[PH:2](=[O:3])([O-:9])[O-:6]

Participants

4

Reactant 2

HCID 962WaterHCID 15455Tetraethyl methylenediphosphonate

Product 1

HCID 178527067HCID 178527067, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
12.5 °C

Procedure

A fixed amount of base and certain solvent (see the table below for the type of base and solvent) are added to a 100 ml three-necked bottle under the protection of nitrogen, 10 ml solvent (the same as the above solvent) with a fixed amount of tetraethyl methylenediphosphonate (see the table below for molar weight) dissolved therein is dropwise added on the condition that magnetic stirring is performed and cold water bath is maintained within a range from 10 to 15° C., gas is discharged, the addition can be finished about half an hour later, and stirring is continued for reaction for 20 minutes. Then, 10 ml solvent (the same as the above solvent), with 2.1 g C-14 aldehyde having a formula (3B) (prepared in the embodiment 7, 0.010 mol) dissolved therein, is dropwise added on the condition that cold water bath is maintained at a particular temperature, the addition can be finished about half an hour later, and stirring is continued while the temperature is maintained for reaction for 20 minutes. 10 ml water and 20 ml ether are 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, the solvent is dried by evaporation under reduced pressure to obtain 3,7,11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate crude product, which is light brown liquid. Measurement for gas phase content and calculation for yield are carried out, and the results are shown in the table below.

Workup

  1. dissolutiondissolved
  2. additiontherein is dropwise added on the condition
  3. additionthe addition
  4. waitcan be finished about half an hour
  5. stirringlater, and stirring
  6. customis continued for reaction for 20 minutes
  7. dissolutiondissolved
  8. additionis dropwise added on the condition that cold water bath
  9. temperatureis maintained at a particular temperature
  10. additionthe addition
  11. waitcan be finished about half an hour
  12. stirringlater, and stirring
  13. temperatureis maintained for reaction for 20 minutes
  14. stirringby stirring for 10 minutes
  15. washlayering, organic layer is rinsed by 20 ml sodium hydride aqueous solution with the concentration of 10%
  16. dry with materialdried by magnesium sulfate
  17. filtrationfiltered
  18. customthe solvent is dried by evaporation under reduced pressure

Sources & evidence

ORD record
ord-60718f86193c454b8e799b9f7dfb3712
Source dataset
uspto-grants-2014_07
Patent number
US08765988B2

Reaction notes

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