Reaction #55869

Reaction equation

Thiophene

trichloroacetaldehyde

→

α-trichloromethyl-2-thiophenemethanol

Yield 20.0%

Solvents

n-heptane

Conditions

Workup

1. 1
   TemperatureThe solution was heated
2. 2
   Temperatureunder reflux for 3.5 hr
3. 3
   TemperatureAfter cooling
4. 4
   Concentrationthe n-heptane solution was concentrated
5. 5
   workup.DISTILLATIONthe residue was purified by distillation

Procedure

Thiophene (4.2 g, 50 mmol) and trichloroacetaldehyde (7.35 g, 50 mmol) were dissolved in n-heptane (25 ml). The solution was heated under reflux for 3.5 hr. under a Soxleht apparatus in which Amberlyst 15 (4.2 g) had been placed. After cooling, the n-heptane solution was concentrated, and the residue was purified by distillation to give 2.32 g of α-trichloromethyl-2-thiophenemethanol boiling at 98°-100° C./1.0 mmHg.

Source