Hydrogen Sulfide → 2,6-Octadiene-1-thiol, 3,7-dimethyl-

HRID 2164178Notes

Reaction equation

HRID 2164178 reaction equation
[OH-].[Na+].CO.[SH2:5].Br[CH2:7][CH:8]=[C:9]([CH3:16])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14]>O>[CH3:16][C:9]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:8][CH2:7][SH:5]

Participants

6

Reactant 4

HCID 402Hydrogen Sulfide2×HCID 887MethanolHCID 14798Sodium HydroxideHCID 802281-Bromo-3,7-dimethylocta-2,6-diene

Product 1

HCID 619832,6-Octadiene-1-thiol, 3,7-dimethyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2 g. of sodium hydroxide in 40 ml. of methanol saturated with hydrogen sulfide is added 14 g. of 1-bromo-3,7-dimethylocta-2,6-diene. The mixture is stirred at about 25° for about five hours with continued introduction of hydrogen sulfide. The mixture is diluted with water and then extracted with petroleum ether. The organic phase is washed well with water, dried over sodium sulfate and evaporated under reduced pressure to yield 3,7-dimethylocta-2,6-dienylmercaptan which is purified by chromatography.

Workup

  1. extractionextracted with petroleum ether
  2. washThe organic phase is washed well with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-dd06e1bddc844115a8d66db40303febd
Source dataset
uspto-grants-1979_01
Patent number
US04137273

Reaction notes

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