Sodium Hydroxide → HCID 178528005, compound

HRID 259291Notes

Reaction equation

HRID 259291 reaction equation
[CH:1]1([SH:7])[CH2:6][CH2:5][CH2:4][CH2:3]C1.[OH-].[Na+].O1[CH2:15][CH2:14]OCC1.Cl[CH2:17][C:18]([C-:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1)=O.[CH-:25]1C=[CH:28][CH:27]=[CH:26]1.[Fe+2:30]>O>[CH:15]1([CH2:17][C:18]([C-:20]2[CH:24]=[CH:23][CH:22]=[CH:21]2)=[S:7])[CH2:14][CH2:28][CH2:27][CH2:26][CH2:25]1.[CH-:3]1[CH:4]=[CH:5][CH:6]=[CH:1]1.[Fe+2:30]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 15290CyclohexanethiolHCID 312751,4-DioxaneHCID 178520780HCID 178520780, compound

Product 1

HCID 178528005HCID 178528005, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

Cyclohexylmercaptan (11.6g, 0.1M) was added to a solution of sodium hydroxide (4g, 0.1M) in water (20 ml). Dioxan (300 ml) was added and the resulting white precipitate was redissolved on the addition of a further small quantity of water. Chloroacetylferrocene (27.3g, 0.1M) was then added and the reaction mixture was heated at 100° for 2 hours with stirring. The cooled reaction mixture was diluted with water and extracted with chloroform. The organic layer was washed with water, dried over anhydrous sodium sulphate and concentrated by rotary evaporation. The crystalline product obtained was purified by recrystallisation from petroleum ether (40-60), but needed column chromatography on silica gel with petroleum ether (60-80)-ethyl acetate (9:1) for final purification. Orange needles of the title compound were thus obtained (6.4g) mp = 89°.

Workup

  1. temperaturethe reaction mixture was heated at 100° for 2 hours
  2. customThe cooled reaction mixture
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated by rotary evaporation
  7. customThe crystalline product obtained
  8. customwas purified by recrystallisation from petroleum ether (40-60)
  9. custompurification

Sources & evidence

ORD record
ord-1d0955d824454bedaa997fc50f2811ac
Source dataset
uspto-grants-1977_07
Patent number
US04036983

Reaction notes

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