Potassium Hydroxide → Phosphorothioic acid, O,O-dipropyl ester, potassium salt

HRID 1080618Notes

Reaction equation

HRID 1080618 reaction equation
[CH2:1]([O:4][P:5](Cl)([O:7][CH2:8][CH2:9][CH3:10])=[S:6])[CH2:2][CH3:3].[OH-:12].[K+:13]>C(O)CC>[K+:13].[P:5]([O-:12])([O:7][CH2:8][CH2:9][CH3:10])([O:4][CH2:1][CH2:2][CH3:3])=[S:6]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 75651Phosphorochloridothioic acid, O,O-dipropyl ester

Product 1

HCID 23678814Phosphorothioic acid, O,O-dipropyl ester, potassium saltYield 61.6%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

To 100 g (460 mmole) of di-n-propylchlorothiophosphate in 300 ml of 1-propanol was added 58.8 g (920 mmole) of 88% potassium hydroxide pellets. The reaction mixture was refluxed overnight and then cooled to room temperature. The precipitated potassium chloride was filtered off and the solvent was stripped in vacuo. The resulting solid was slurried in 20% diethyl ether/80% hexanes and filtered yielding 67 g of the title compound, a fluffy white solid, mp 205°-207° C.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. filtrationThe precipitated potassium chloride was filtered off
  3. filtrationfiltered

Sources & evidence

ORD record
ord-4fbd73ee538b474d94233b94bf6280b7
Source dataset
uspto-grants-1996_12
Patent number
US05583124

Reaction notes

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