2-Mercaptoethanol → 2-Piperonylthioethanol

HRID 2398802Notes

Reaction equation

HRID 2398802 reaction equation
[H-].[Na+].[SH:3][CH2:4][CH2:5][OH:6].[CH2:7](Br)[C:8]1[CH:16]=[CH:15][C:14]2[O:13][CH2:12][O:11][C:10]=2[CH:9]=1.CCOCC>O1CCCC1.O>[CH2:7]([S:3][CH2:4][CH2:5][OH:6])[C:8]1[CH:16]=[CH:15][C:14]2[O:13][CH2:12][O:11][C:10]=2[CH:9]=1

Participants

7

Reactant 4

HCID 15672-MercaptoethanolHCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 64514231,3-Benzodioxole, 5-(bromomethyl)-

Product 1

HCID 214340522-Piperonylthioethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent4×

Procedure

0.96 g (0.02 mol) of 50% sodium hydride dispersion are freed from the mineral oil with absolute tetrahydrofuran and suspended in 30 cc of tetrahydrofuran. A solution of 1.56 g (0.02 mol) of 2-mercaptoethanol in 10 cc of tetrahydrofuran is added at 20°-25° while stirring, to this suspension. The mixture is stirred at 60° over the course of 10 hours. After this period a solution of 4.3 g (0.02 mol) of piperonyl bromide in 30 cc of tetrahydrofuran is added dropwise to the mixture. The reaction mixture is stirred at 60° over the course of 8 hours, subsequently cooled to 20° and 100 cc amounts of ether and water are added. The organic phase is separated off in a separating funnel, extracted with saturated sodium chloride solution, dried over sodium sulphate and evaporated. The residue may be purified by chromatography on silica gel with hexane/ethyl acetate (1:2). 2-Piperonylthio-ethanol is obtained as a colourless oil, which according to gas-chromatography is pure.

Workup

  1. stirringThe mixture is stirred at 60° over the course of 10 hours
  2. stirringThe reaction mixture is stirred at 60° over the course of 8 hours
  3. temperaturesubsequently cooled to 20°
  4. customThe organic phase is separated off in a separating funnel
  5. extractionextracted with saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customThe residue may be purified by chromatography on silica gel with hexane/ethyl acetate (1:2)

Sources & evidence

ORD record
ord-aadafa4df7044dd09373becc60779539
Source dataset
uspto-grants-1977_05
Patent number
US04025641

Reaction notes

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