5,6-dihydro-2H-pyran-3-carbaldehyde Chemical Properties

Boiling point:

49.2 °C

Density 

1.114 g/cm3

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C6H8O2/c7-4-6-2-1-3-8-5-6/h2,4H,1,3,5H2

InChIKey

RKXCKEHBMLDWET-UHFFFAOYSA-N

SMILES

C1OCCC=C1C=O

Safety Information

HazardClass 

IRRITANT

5,6-dihydro-2H-pyran-3-carbaldehyde Usage And Synthesis

Uses

5,6-Dihydro-2H-pyran-3-carboxaldehyde is a useful synthetic intermediate and a derivative of acrolein (A191200); a compound well-known for its use in the synthesis of acrylic acid.

Synthesis

Acrolein [stabilized] (40 g, 713 mmol) was dissolved in a solvent mixture of dichloromethane (105 mL) and deionized water (2.3 mL) at room temperature and stirred to form a homogeneous mixture. Phosphoric acid (12.7 mL) was slowly added dropwise to the above mixture. The reaction system was heated to reflux and the reaction was continued overnight. Upon completion of the reaction, the reaction mixture was purified by reduced pressure distillation (110-150 °C, 20 mmHg) to afford the target product 5,6-dihydro-2-H pyran-3-carbaldehyde (12.6 g, 15.7% yield). Mass spectrometry result (m/z): [M + H]+ 113.1.

References

[1] Monatshefte fuer Chemie, 1990, vol. 121, # 11, p. 963 - 970
[2] New Journal of Chemistry, 2008, vol. 32, # 8, p. 1354 - 1358
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 23, p. 6072 - 6075
[4] Angew. Chem., 2013, vol. 125, # 23, p. 6188 - 6191
[5] Patent: WO2016/85939, 2016, A2. Location in patent: Paragraph 00259

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