1-Dodecanethiol → Ethanol, 2-(dodecylthio)-

HRID 1700929Notes

Reaction equation

HRID 1700929 reaction equation
Br[CH2:2][CH2:3][OH:4].[CH2:5]([SH:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C1(C)C=CC=CC=1>[CH2:5]([S:17][CH2:2][CH2:3][OH:4])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 81951-DodecanethiolHCID 108982-BromoethanolHCID 11430Potassium Carbonate

Product 1

HCID 73835Ethanol, 2-(dodecylthio)-Yield 77%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
22 °C

Procedure

A mixture of 2-bromoethanol (6.08 g, 48.7 mmol), dodecanethiol (9.86 g, 48.7 mmol) and potassium carbonate (11 g) in dry N,N-dimethylformamide (100 ml) was stirred at 22° C. for 10 h. The reaction mixture was then diluted with toluene (400 ml) washed with water and dried (magnesium sulfate). The solvent was evaporated under reduced pressure and the residue was filtered through a silica gel pad (toluene-ethyl acetate 95:5) and distilled under vacuum to give 9.18 g (77%) of 2-(dodecylthio)ethanol as a clear oil which solidified on standing: b.p. 100-105° C./0.01 torr (bulb to bulb distillation, air bath temperature); m.p. 31-32° C.

Workup

  1. washwashed with water
  2. dry with materialdried (magnesium sulfate)
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationthe residue was filtered through a silica gel pad (toluene-ethyl acetate 95:5)
  5. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-e9c06d325625480ea2a0933450fc5ea0
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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