Epibromohydrin → 1,3-Bis(4'-methylbenzylthio)-2-propanol

HRID 259272Notes

Reaction equation

HRID 259272 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Br.[CH3:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][SH:12])=[CH:9][CH:8]=1.[H-].[Na+]>O1CCCC1>[CH3:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][S:12][CH2:1][CH:3]([OH:5])[CH2:4][S:12][CH2:11][C:10]2[CH:13]=[CH:14][C:7]([CH3:6])=[CH:8][CH:9]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 782524-Methylbenzyl mercaptan

Product 1

HCID 214237301,3-Bis(4'-methylbenzylthio)-2-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Epibromohydrin (1.37 g.) in 2 ml. dry tetrahydrofuran is added to a stirred suspension of the salt obtained by mixing 3 g. of 4-methylbenzyl mercaptan and 550 mg. of sodium hydride (56% dispersion in mineral oil) in 60 ml. dry tetrahydrofuran. The resulting solution is heated at reflux for 4 hours. Thereafter, the solvent is removed and 30 ml. of water is added to the residue. The resultant aqueous mixture is extracted with ether and the ether extracts washed with water, dried over magnesium sulfate and evaporated to dryness to yield 1,3-bis(4'-methylbenzylthio)-2-propanol.

Workup

  1. customobtained
  2. additionby mixing 3 g
  3. temperatureThe resulting solution is heated
  4. temperatureat reflux for 4 hours
  5. customThereafter, the solvent is removed
  6. additionof water is added to the residue
  7. extractionThe resultant aqueous mixture is extracted with ether
  8. washthe ether extracts washed with water
  9. dry with materialdried over magnesium sulfate
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-785573d3478846f68223b52921277ede
Source dataset
uspto-grants-1977_07
Patent number
US04036970

Reaction notes

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