Reaction #10706

Reaction equation

N2

3,4-dimethoxythiophene

toluene

(S)-1,2-dodecanediol

→

product

Yield 68.8%

2-n-decyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine

Yield 68.8%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Washwashed with NaHCO3
2. 2
   Concentrationthe organic phase was concentrated
3. 3
   FiltrationSubsequent filtration over SiO2

Procedure

A solution of 3,4-dimethoxythiophene (1.90 g), toluene (30 ml), (S)-1,2-dodecanediol (2.50 g) and p-toluenesulfonic acid monohydrate (100 mg) was heated at 95° C., continuously leading a N2-stream over the solution. After 24 h the reaction mixture was poured into ethyl acetate, washed with NaHCO3 and the organic phase was concentrated. Subsequent filtration over SiO2 using n-hexane/CH2Cl2 (98/2) as eluant resulted in pure product (2.40 g).

Source