Sodium Iodide → Dimethyl acetyl phosphate

HRID 1741762Notes

Reaction equation

HRID 1741762 reaction equation
[P:1]([O-:7])([O:5][CH3:6])([O:3][CH3:4])=[O:2].[Na+].P(OC)(OC)(OC)=O.[I-].[Na+].[C:19](Cl)(=[O:21])[CH3:20]>O1CCCC1>[P:1]([O:7][C:19](=[O:21])[CH3:20])([O:5][CH3:6])([O:3][CH3:4])=[O:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6367Acetyl chlorideHCID 10541Trimethyl PhosphateHCID 23663684Sodium dimethyl phosphate

Product 1

HCID 14665382Dimethyl acetyl phosphateYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of sodium dimethyl phosphate (14.8 g, 0.1 mmol, from trimethyl phosphate and sodium iodide and acetyl chloride (7.8 g, 0.1 mmol) in dry tetrahydrofuran (80 mn) was stirred for two days at room temperature in a flask fitted with a drying tube. The reaction solution was filtered and the tetrahydrofuran was removed under reduced pressure. The resulting colorless liquid was Kugelrohr-distilled (Aldrich Kugelrohr apparatus, 55°-60° C. 0.30 torr) to give 14.2 g (80%) of dimethyl acetyl phosphate.

Workup

  1. customfitted with a drying tube
  2. filtrationThe reaction solution was filtered
  3. customthe tetrahydrofuran was removed under reduced pressure
  4. distillationThe resulting colorless liquid was Kugelrohr-distilled (Aldrich Kugelrohr apparatus, 55°-60° C. 0.30 torr)

Sources & evidence

ORD record
ord-066fbcfb554c4382980d8c292f3fdf83
Source dataset
uspto-grants-1994_08
Patent number
US05334707

Reaction notes

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