Hydrogen Sulfide → HCID 54295110, compound

HRID 1604863Notes

Reaction equation

HRID 1604863 reaction equation
C[O-].[Na+].[Na].[CH3:5][O:6][C:7](=[O:16])[CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[SH2:17]>CO>[CH3:5][O:6][C:7](=[O:16])[CH2:8][CH:9]([SH:17])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 402Hydrogen Sulfide2×HCID 8136Methyl 2-nonenoateHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 54295110HCID 54295110, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A sodium methylate solution is freshly prepared from 0.3 g of sodium and 5 ml of methanol. 10 g of 2-nonenoic acid methyl ester are added to this solution and the mixture is cooled to -70°. After reaching this temperature, 20 ml of hydrogen sulphide are condensed in and the whole batch is transferred into a pre-cooled autoclave. The pressure-vessel is sealed and immediately heated at 50° in an oil-bath for 3 hours. The autoclave is subsequently cooled to room temperature, the excess hydrogen sulphide vented off and the reaction mixture washed with saturated common salt solution and dried. There are obtained 12.4 g of crude product which, after distillation, yields 5.7 g of pure 3-mercaptononanoic acid methyl ester of boiling point 70°/0.2 mm Hg, nD20 1.4602.

Workup

  1. temperaturethe mixture is cooled to -70°
  2. customcondensed in and the whole batch
  3. customThe pressure-vessel is sealed
  4. temperatureimmediately heated at 50° in an oil-bath for 3 hours
  5. washthe reaction mixture washed with saturated common salt solution
  6. customdried
  7. customThere are obtained 12.4 g of crude product which
  8. distillationafter distillation

Sources & evidence

ORD record
ord-d3c1727b10f84dd3aa074f6d2d79bd92
Source dataset
uspto-grants-1976_04
Patent number
US03948816

Reaction notes

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