4-FORMYLCINNAMIC ACID METHYL ESTER Chemical Properties

Melting point:

79-82 ºC

Boiling point:

334.1±25.0 °C(Predicted)

Density 

1.173

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

Pale Yellow

InChI

InChI=1S/C11H10O3/c1-14-11(13)7-6-9-2-4-10(8-12)5-3-9/h2-8H,1H3/b7-6+

InChIKey

KVXMLLMZXPRPNG-VOTSOKGWSA-N

SMILES

C(OC)(=O)/C=C/C1=CC=C(C=O)C=C1

Safety Information

WGK Germany 

3

HS Code 

2918300090

4-FORMYLCINNAMIC ACID METHYL ESTER Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

Cinnamic Acid derivative

Synthesis Reference(s)

Synthesis, p. 747, 1984 DOI: 10.1055/s-1984-30956

Synthesis

GENERAL PROCEDURE: To a 25 mL round-bottomed flask was added p-chlorobenzaldehyde (1.00 mmol), methyl acrylate (0.130 g, 1.50 mmol), triethylamine (0.152 g, 1.50 mmol) and N,N-dimethylformamide (DMF, 5 mL). DMF solution containing catalyst (catalyst concentrations of 0.1, 0.01 and 0.001 mol%, see Table 1; 0.01 mol%, see Table 2) was added to the above mixture via syringe. The flask was assembled to a water condenser with an anhydrous calcium chloride drying tube, and the reaction mixture was continuously stirred and heated in an oil bath at 90°C for 3 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature and subsequently poured into distilled water (300 mL). The product in the aqueous phase was extracted with ethyl acetate (5 x 50 mL). The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product as an oil. Purification of the crude product by silica gel column chromatography (eluent hexane/ethyl acetate, gradient from 10/0 to 8/2, v/v) gave methyl 3-(4-formylphenyl)acrylate as shown in Tables 1 and 2.

References

[1] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 8036 - 8041
[2] Polyhedron, 2018, vol. 151, p. 313 - 322
[3] Tetrahedron Letters, 2011, vol. 52, # 37, p. 4782 - 4787
[4] New Journal of Chemistry, 2016, vol. 40, # 2, p. 1250 - 1255
[5] ChemCatChem, 2013, vol. 5, # 8, p. 2418 - 2424

4-FORMYLCINNAMIC ACID METHYL ESTER(58045-41-3)Related Product Information

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