Hydrogen Sulfide → HCID 13247942, compound

HRID 330120Notes

Reaction equation

HRID 330120 reaction equation
C([O-])(=O)C.[Na+].[SH2:6].[C:7]([C:10]([C:12]([CH3:14])=[CH2:13])=[O:11])([CH3:9])=[CH2:8]>C(O)C>[CH3:13][CH:12]1[C:10](=[O:11])[CH:7]([CH3:9])[CH2:8][S:6][CH2:14]1

Participants

5

Reactant 3

HCID 402Hydrogen Sulfide2×HCID 517045Sodium AcetateHCID 147236112,4-Dimethylpenta-1,4-dien-3-one

Product 1

HCID 13247942HCID 13247942, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2 g. of sodium acetate and 25 ml. of ethanol was saturated with hydrogen sulfide gas. To this was added 7.0 g. (0.063 mole) diisopropenylketone while cooling in an ice bath until the reaction was no longer exothermic. The mixture was stirred at room temperature while passing hydrogen sulfide through the mixture for four hours then allowed to stand overnight. The ethanol and excess H2S were evaporated in vacuo and the residue taken up in ethyl ether, washed in turn with water, potassium carbonate solution, dilute hydrochloric acid, and water again. The ether extracts were dried (Na2SO4) and evaporated to provide 6.8 g. of oil. This was distilled in vacuo through a 10 cm. Vigreaux column to provide 1.67 g. of product, B.P. 83°-86° C./9 mm. which was used in the next step without further purification.

Workup

  1. additionA mixture of 2 g
  2. additionTo this was added 7.0 g
  3. customfor four hours
  4. customThe ethanol and excess H2S were evaporated in vacuo
  5. washwashed in turn with water, potassium carbonate solution, dilute hydrochloric acid, and water again
  6. dry with materialThe ether extracts were dried (Na2SO4)
  7. customevaporated
  8. customto provide 6.8 g
  9. distillationThis was distilled in vacuo through a 10 cm
  10. customVigreaux column to provide 1.67 g
  11. customwhich was used in the next step without further purification

Sources & evidence

ORD record
ord-f1e6ba6b7c5e41a0a8c20e39f4e07682
Source dataset
uspto-grants-1990_01
Patent number
US04894464

Reaction notes

Loading…