Reaction #985291

Reaction equation

potassium carbonate

decyl bromide

mercaptoethanol

→

2-(decylthio)ethanol

Yield 94.0%

Solvents

acetone

Conditions

Workup

1. 1
   Otherpartitioned between water and 80% hexane/ethyl acetate
2. 2
   WashThe organic phase was washed with 2N sodium hydroxide
3. 3
   Dryingdried over magnesium sulfate
4. 4
   Otherthe volatiles removed under vacuum

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.

Source