7281. α-Phenylcinnamic Acid

Nomenclature

CAS number: 3368-16-9
α-(Phenylmethylene)benzeneacetic acid; 2,3-diphenylacrylic acid; 2,3-diphenylpropenoic acid; stilbene-α-carboxylic acid.
C15H12O2; mol wt 224.25.
C 80.34%, H 5.39%, O 14.27%.

Description and references

Prepn of cis-form: Buckles, Hausman, J. Am. Chem. Soc. 70, 415 (1948); Buckles, J. Chem. Educ. 27, 210 (1950); Buckles, Bremer, Org. Synth. coll. vol. IV, 777 (1963); B. H. Patwardhan, G. Bagavant, Indian J. Chem. 10, 59 (1972). Prepn of cis- and trans-forms: L. F. Fieser, Experiments in Organic Chemistry (Heath, Boston, 3rd ed., 1955) p 182. Isomerization studies: S. V. Kessar et al., Indian J. Chem. 20B, 4 (1981).

Chemical structure

Derivative

cis-Form.

Nomenclature

CAS number: 91-47-4

Properties

Silky needles from ether + petr ether, mp 174°. pKa 6.1 in 60% ethanol. uv max (ethanol): 223, 280 nm (ε 32100, 19500). Sol in hot water, methanol, ethanol, isopropanol, ether, benzene.

Derivative

trans-Form.

Nomenclature

CAS number: 91-48-5

Properties

Stout prisms from ether + petr ether, mp 138-139°. Less stable than the cis-form. pKa 4.8 in 60% ethanol. uv max (ethanol): 222, 289 nm (ε 14500, 22500). More sol than the cis-form.