Phenyl cinnamate

The a-carbon atom of the phenylacetyl group is more susceptible to attack by the basic catalyst (triethylamine) than the acetyl group hence a-phenyl-cinnamic acid, but no cinnamic acid, is obtained. 

Chapter IV. a-Chloromethylnaphthalene (IV,23) benzylamine (Gabriel synthesis) (IV,39) i r.N -dialkylanilines (from amines and trialkyl orthophosphates) (IV,42) a-naphthaldehyde (Sommelet reaction) (IV,120) a-phenyl-cinnamic acid (Perkin reaction using triethylamine) (IV,124) p-nitrostyrene (IV,129) p-bromonaphthalene and p naphthoic acid (from 2 naphthylamine-1 -sulphonic acid) (IV,62 and IV,164) diphenic acid (from phenanthrene) (IV,165). 

Table 2-4 gives data for the alkaline hydrolysis of phenyl cinnamate under pseudo-first-order conditions, with calculations made in order to apply the Guggenheim method. The plot according to Eq. (2-55) is shown in Fig. 2-9. From the slope the pseudo-first-order rate constant is 3.37 x 10 s . ... 

Table 2-4. Application of Guggenheim s Method to the Hydrolysis of Phenyl Cinnamate ...

Figure 2-10. Plot of Eq. (2-56) for the hydrolysis of phenyl cinnamate. Data are from Table 2-4.

The kinetics of alkaline hydrolysis of phenyl cinnamate were studied at 25°C, in solutions containing 0.8% acetonitrile ionic strength, 0.3 M initial ester, 8.19 X 10- M reaction followed spectrophotometrically in 5-cm cells at 295 nm. For studies at three pH values, these absorbance data were obtained. The pH was established with sodium hydroxide of the normality specified in the heading of the table (as titrimetrically determined). 

It is primarily the prospect of reduced mobility and volatility, with the expected improvement in long-term performance, which motivates the preparation of polymeric ultraviolet stabilizers. Work in this area was reviewed thoroughly by Bailey and Vogl in 1976 (1), and more recently by the author (2). The present paper describes recent synthetic work involving four classes of effective ultraviolet stabilizers salicylate esters (I), 2-hydroxybenzophenones (II), a-cyano-3-phenyl-cinnamates (III) and hydroxyphenylbenzotriazoles (IV). In each... 

Radical polymerizations of vinyl-substituted ultraviolet stabilizers were accomplished with azobisisobutyronitrile (AIBN) as initiator, with careful exclusion of oxygen. Copolymerization was also readily achieved. The following sections describe in detail the preparation of polymeric ultraviolet stabilizers from salicylate esters, 2-hydroxybenzophenones, a-cyano-p-phenyl-cinnamates and hydroxyphenylbenzotriazoles. 

Phenyl cinnamate and other phenolic esters have been prepared by heating the acid and phenol in the presence of phosphorus oxychloride,1 and by heating the acid anhydride and phenol together in the presence of a dehydrating agent such as fused zinc chloride or anhydrous sodium acetate.2 Phenyl cinnamate has also been prepared by the careful distillation of phenyl fumarate.3... 

Phenylbenzbyldiazomethane, 48 Phenyl cinnamate, 77 o-Phenylenediamine, 10 Phosphorus oxychloride, 11 Phosphorus trichloride, 106 Photoflood lamps, 84, 104 Phthalic anhydride, 70 Phthalic monoperacid, 70 Phthaloyl chloride, 51 a-Picoline, 79... 

Neither the anilide of cinnamic acid94 nor the diphenyl substituted acroyl anilide 138 95 yields any product of rearrangement or cyclodimerization. Upon irradiation of 138 in benzene solution in a Pyrex reactor, only the isomeric /9-lactams 139 (2.3%) and 140 (37%), in addition to dihydrocarbostyril 141 (5%), were isolated. The latter is the major product upon irradiation of alkyl substituted acroyl anilides.96 On the other hand, the closely related phenyl cinnamate rearranges regularly to the ortho- and para-positions97 and does not dimerize as the other alkyl esters of cinnamic acid.98... 

Phenyl cinnamate [2757-04-2] M 224.3, m 75-76°, b 205-207°/15mm. Crystd from EtOH (2ml/g). It can also be distd under reduced pressure. 

Phenyl cinnamate, 780, 784 a-Phenylcinnniiac acid, 707, 708, 713 Phenyldiazonium chloride, solid, 591, 597... 

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