2,3-Dihydrothieno[3,4-b][1,4]dioxine-5-carbaldehyde

Chemical Properties

Gray crystal

Synthesis

General procedure for the synthesis of 2-(3,4-ethenyldioxythiophene) formaldehyde from N,N-dimethylformamide (DMF) and 3,4-ethenyldioxythiophene (EDOT): to a mixture containing EDOT (15.0 g, 0.1 mol) and DMF (11.0 g, 0.15 mol) was added slowly and dropwise at 0 °C a mixture of 2-(3,4-ethenyldioxythiophene) and 3,4-ethenyldioxythiophene (EDOT) dissolved in anhydrous dichloromethane ( 80 mL) in triphosgene (BTC, 11.9 g, 0.04 mol). The reaction mixture was warmed to 35 °C and stirred continuously for 1 h. Subsequently, it was cooled to room temperature and poured into ice water (250 mL). The pH of the aqueous phase was adjusted to 7-8 with 10% sodium hydroxide solution and the organic phase was separated. The aqueous phase was extracted three times with dichloromethane. All organic phases were combined and dried with anhydrous magnesium sulfate. After removal of the solvent by distillation under reduced pressure, the crude product was recrystallized by 95% ethanol to give a white needle-like crystal product (15.5 g, 86.3% yield). The product was characterized by 1H NMR (400 MHz): δ/ppm: 9.90 (s, 1H), 6.79 (s, 1H), 4.38-4.25 (m, 4H).

References

[1] Advanced Functional Materials, 2011, vol. 21, # 4, p. 634 - 643
[2] Tetrahedron, 1999, vol. 55, # 40, p. 11745 - 11754
[3] Journal of the American Chemical Society, 2004, vol. 126, # 50, p. 16440 - 16450
[4] Physical Chemistry Chemical Physics, 2015, vol. 17, # 8, p. 5776 - 5784
[5] Russian Journal of Applied Chemistry, 2010, vol. 83, # 8, p. 1435 - 1439