1-Bromodecane → 2-(Decylthio)ethanol

HRID 643239Notes

Reaction equation

HRID 643239 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7](Br)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[SH:18][CH:19](O)C>CC(C)=O>[CH2:7]([S:18][CH2:19][CH2:1][OH:4])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 81731-BromodecaneHCID 11430Potassium CarbonateHCID 4713212Mercapto-ethanol

Product 1

HCID 966542-(Decylthio)ethanolYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under nitrogen, to a suspension of potassium carbonate (27 g, 200 mmol) in acetone (100 ml) was added decyl bromide (10 ml, 50 mmol) and mercaptoethanol (4.4 ml, 63 mmol). The suspension was stirred at room temperature for 2 days, then partitioned between water and 80% hexane/ethyl acetate. The organic phase was washed with 2N sodium hydroxide, dried over magnesium sulfate, and the volatiles removed under vacuum to give 2-(decylthio)ethanol (10.2 g, 47 mmol) as a colorless liquid that was used without further purification.

Workup

  1. custompartitioned between water and 80% hexane/ethyl acetate
  2. washThe organic phase was washed with 2N sodium hydroxide
  3. dry with materialdried over magnesium sulfate
  4. customthe volatiles removed under vacuum

Sources & evidence

ORD record
ord-145393533a6f486480d6ad898ddc5c64
Source dataset
uspto-grants-2010_04
Patent number
US07700550B2

Reaction notes

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