Hydrochloric Acid → HCID 12858247, compound

HRID 1285232Notes

Reaction equation

HRID 1285232 reaction equation
[H-].[Na+].[C:3]1([PH:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>CN(C)C=O>[C:3]1([P:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)([C@@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]2[P:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:16])=[O:16])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 254003Diphenylphosphine oxide

Product 1

HCID 12858247HCID 12858247, compoundYield 138.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.34 g; 14.16 mmol) was added to a stirred solution of diphenylphosphine oxide (2.8 g; 13.86 mmol) in dimethylformamide (30 ml) at room temperature under argon. To the yellow solution was then added cyclohexane epoxide (0.68 g; 6.94 mmol) and the reaction mixture was warmed to 70° C. The yellow color slowly faded and after 2 hours a white precipitate had formed. The mixture was cooled, acidified with dilute HCl and the product extracted with chloroform. The removal of all solvents afforded, after recrystallization from chloroformdiethylether, trans-1,2-bis(diphenylphosphinyl)cyclohexane (3.10 g; 93% yield).

Workup

  1. customa white precipitate had formed
  2. temperatureThe mixture was cooled
  3. extractionthe product extracted with chloroform
  4. customThe removal of all solvents
  5. customafforded

Sources & evidence

ORD record
ord-f5d0c0e347d84b848d02eeb7fe1e9842
Source dataset
uspto-grants-1986_01
Patent number
US04565892

Reaction notes

Loading…