1-Dodecanethiol → 1,3-Bis(dodecylsulfanyl)propan-2-ol

HRID 567186Notes

Reaction equation

HRID 567186 reaction equation
[CH2:1]([SH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Na].[CH2:15]([CH:17]1[O:19][CH2:18]1)Br>C(O)C.CCOCC>[CH2:1]([S:13][CH2:15][CH:17]([OH:19])[CH2:18][S:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 81951-DodecanethiolHCID 18430EpibromohydrinHCID 5360545Sodium

Product 1

HCID 158395031,3-Bis(dodecylsulfanyl)propan-2-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

26.6 ml Dodecanethiol was added to an ethylate solution of 2.6 g sodium in 100 ml ethanol and the solution was stirred for 1 hour at room temperature. Then 8.5 ml epibromohydrin was added dropwise within 30 min and stirred overnight. The residue was taken up in ether after removing the solvent, washed twice with water and dried. The desired compound crystallized on evaporation of the solution. Yield 28.5 g (62%).

Workup

  1. stirringstirred overnight
  2. customafter removing the solvent
  3. washwashed twice with water
  4. customdried
  5. customThe desired compound crystallized on evaporation of the solution

Sources & evidence

ORD record
ord-9056b7813aa146589d3b2174d64054f7
Source dataset
uspto-grants-2001_01
Patent number
US06177469B1

Reaction notes

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