4-ethoxy-1,1,1-trichloro-3-buten-2-one Chemical Properties

Boiling point:

200℃

Density 

1.368

Flash point:

72℃

InChI

InChI=1S/C6H7Cl3O2/c1-2-11-4-3-5(10)6(7,8)9/h3-4H,2H2,1H3

InChIKey

VKNLVLNOHCTKII-UHFFFAOYSA-N

SMILES

C(Cl)(Cl)(Cl)C(=O)C=COCC

4-ethoxy-1,1,1-trichloro-3-buten-2-one Usage And Synthesis

Synthesis

Under nitrogen protection, 218.4 g (1.2 mol) of trichloroacetyl chloride was added to a dry round-bottomed flask and the flask was cooled to 0 °C in an ice bath. Subsequently, 172.8 g (2.4 mol) of ethyl vinyl ether was slowly added dropwise to the flask and the reaction temperature was maintained at 0 °C. The reaction mixture was stirred thoroughly under nitrogen atmosphere. After that, the reaction system was slowly warmed to 30 °C and stirring was continued at this temperature for 10 hours to ensure complete reaction. After completion of the reaction, the reaction mixture was refluxed for 3 hours. Finally, the product was purified by distillation under reduced pressure to afford 247.2 g of 1,1,1-trichloro-4-ethoxy-3-buten-2-one as a pale yellow oil (boiling point 117-119 °C, pressure 13 mmHg) in 96.5% yield.

References

[1] Patent: CN107056608, 2017, A. Location in patent: Paragraph 0023; 0024
[2] Chemische Berichte, 1982, vol. 115, p. 2766 - 2782
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 254 - 257
[4] Patent: CN105503878, 2016, A. Location in patent: Paragraph 0010
[5] Synlett, 2008, # 11, p. 1684 - 1686

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