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Potassium Hydroxide → Bis [4-[(ethoxy)(propylthio)phosphoryloxy]phenyl]sulfide

HRID 1461978
Notes
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Reaction equation

HRID 1461978 reaction equation
[S:1]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[P:16](=[O:25])(Cl)([S:20][CH2:21][CH2:22][CH3:23])[O:17][CH2:18][CH3:19].[OH-:26].[K+].C1CC2OCCOCCOC3C(OCCO[CH2:51][CH2:52][O:53]C2CC1)CCCC3>C(#N)C>[CH2:18]([O:17][P:16]([O:8][C:5]1[CH:6]=[CH:7][C:2]([S:1][C:9]2[CH:14]=[CH:13][C:12]([O:15][P:16]([O:53][CH2:52][CH3:51])([S:20][CH2:21][CH2:22][CH3:23])=[O:26])=[CH:11][CH:10]=2)=[CH:3][CH:4]=1)([S:20][CH2:21][CH2:22][CH3:23])=[O:25])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 175704,4'-ThiodiphenolHCID 85955Dicyclohexano-18-crown-6HCID 11745722O-Ethyl S-propyl chlorothiophosphate

Product 1

HCID 13343963Bis [4-[(ethoxy)(propylthio)phosphoryloxy]phenyl]sulfide

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

To a 250 ml round bottom flask was added 4,4'-thiodiphenol (4.36 g, 20 mmol), O-ethyl S-n-propyl phosphorochloridothioate (9.12 g, 45 mmol), powdered potassium hydroxide (3.37 g, 60 mmol), dicyclohexano-18-crown-6 (catalytic quantity), and acetonitrile. This mixture was refluxed 14 hours, cooled to room temperature, and the organic soluble fraction decanted from the solids. The organic solution was diluted with ether and successively washed with 4M NaOH (3×100 ml), water (2×50 ml), 5% HCl (1×50 ml), water (2×50 ml), and brine (2×50 ml). After drying (MgSO4) the solution was concentrated under reduced pressure to give a colorless oil (4.8 g, 7.6 mmol).

Workup

  1. temperatureThis mixture was refluxed 14 hours
  2. customthe organic soluble fraction decanted from the solids
  3. additionThe organic solution was diluted with ether
  4. washsuccessively washed with 4M NaOH (3×100 ml), water (2×50 ml), 5% HCl (1×50 ml), water (2×50 ml), and brine (2×50 ml)
  5. dry with materialAfter drying (MgSO4) the solution
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-fc5b32dd410548f1b4fb89eab4fa1bc5
Source dataset
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04457922

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes