Hydrogen Sulfide → HCID 54565844, compound

HRID 1604862Notes

Reaction equation

HRID 1604862 reaction equation
[Na].[CH2:2]([O:4][C:5](=[O:13])[CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH3:3].[SH2:14]>C(O)C>[CH2:2]([O:4][C:5](=[O:13])[CH2:6][CH:7]([SH:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH3:3]

Participants

5

Reactant 3

HCID 402Hydrogen Sulfide2×HCID 23832Ethyl 2-octenoateHCID 5360545Sodium

Product 1

HCID 54565844HCID 54565844, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.2 g of sodium are dissolved in 10 ml of absolute ethyl alcohol. After completed alcoholate-formation, 5 g of 2-octenoic acid ethyl ester are added and the solution is cooled to -70°. At this temperature, 10 ml of hydrogen sulphide are condensed into the solution. Subsequently, the whole mixture is immediately transferred into an autoclave, pre-cooled to about -30°, and left by itself overnight at room temperature in the sealed pressure vessel. On the next morning, the autoclave is heated at 50° for a further 2 hours. After cooling to room temperature, the excess hydrogen sulphide is vented off, the reaction product washed with saturated common salt solution, dried and distilled. There are obtained 1.6 g of 3-mercapto-octanoic acid ethyl ester of boiling point 74°/0.4 mm Hg, nD20 1.4538.

Workup

  1. additionare added
  2. temperaturethe solution is cooled to -70°
  3. customcondensed into the solution
  4. temperaturepre-cooled to about -30°
  5. temperatureOn the next morning, the autoclave is heated at 50° for a further 2 hours
  6. washthe reaction product washed with saturated common salt solution
  7. customdried
  8. distillationdistilled

Sources & evidence

ORD record
ord-c6c55aaeb959431384acbcf80750b46e
Source dataset
uspto-grants-1976_04
Patent number
US03948816

Reaction notes

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