Acetone → Dibutyl (2-hydroxypropan-2-yl)phosphonate

HRID 13741Notes

Reaction equation

HRID 13741 reaction equation
Cl.[P:2]([O-:13])([O:8][CH2:9][CH2:10][CH2:11][CH3:12])[O:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:14][C:15]([CH3:17])=[O:16]>C(N(CC)CC)C.[Cl-].[Mg+2].[Cl-]>[CH2:4]([O:3][P:2]([C:15]([OH:16])([CH3:17])[CH3:14])(=[O:13])[O:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 23414612Dibutylphosphite

Product 1

HCID 240276Dibutyl (2-hydroxypropan-2-yl)phosphonateYield 91.7%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 5360315Magnesium ChlorideCatalyst

Conditions

Temperature
80 °C

Procedure

Next, into a two-liter four-necked flask provided with a stirrer, a thermometer, a dropping device, a hydrochloric-acid-recovering device and a condenser, 213.4 g (1.1 moles) of dibutyl phosphite, 5.6 g (0.06 moles) of triethylamine and 1.9 g (0.020 moles) of magnesium chloride were fed. While stirring the resulting mixed solution at 40° C., 70.2 g (1.2 moles) of acetone was added thereto in an hour. The mixed solution was further stirred for 1 hour at the same temperature (40° C.) to complete the reaction. Thereafter, the resulting reaction solution was washed with a 1% dilute hydrochloric acid aqueous solution and a saturated sodium carbonate aqueous solution successively and rinsed with water twice to remove the triethylamine and the magnesium chloride. Then, while heating the reaction mixture to 80° C., water was recovered under a reduced pressure of about 2.7 kPa. Further, nitrogen topping was carried out under the same conditions to remove the low-boiling point portions, thereby obtaining 254.6 g of dibutyl(1-hydroxy-1-methylethyl)phosphonate (raw material 2).

Workup

  1. customNext, into a two-liter four-necked flask provided with a stirrer
  2. additionmixed solution at 40° C.
  3. waitin an hour
  4. stirringThe mixed solution was further stirred for 1 hour at the same temperature (40° C.)
  5. customthe reaction
  6. customThereafter, the resulting reaction solution
  7. washwas washed with a 1% dilute hydrochloric acid aqueous solution
  8. washa saturated sodium carbonate aqueous solution successively and rinsed with water twice
  9. customto remove the triethylamine
  10. customwater was recovered under a reduced pressure of about 2.7 kPa
  11. customto remove the low-boiling point portions

Sources & evidence

ORD record
ord-0ea2bdc4c866408ab508898c07c300dd
Source dataset
uspto-grants-2010_06
Patent number
US07728162B2

Reaction notes

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