3-phenylpropionic acid 3-phenylpropanoic

Beilstein Handbook Reference) AI3-00892 Benzenepropanoic acid Benzeneproplonic acid Benzylacetic acid BRN 0907515 CCRIS 3199 Dihydrocinnamic acid EINECS 207-924-5 FEMA No. 2889 Hydrocinnamic acid NSC 9272 Phenylpropanoic acid 3-Phenylpropanoic acid p-Phenylpropionic acid 3-Phenylpropionic acid. Fixative for perfumes, flavoring. Solid mp = 47-48° bp n 280° Xm = 247, 252, 257, 260, 263, 267 nm (MeOH) soluble in H2O (5.8 g/l), EtOH, Et20, CCl4, CHCI3, CS2, very soluble in CeHe, Greeff R.W. Co. Janssen Chimica Penta Mfg. 

Synonyms Benzenepropanoic acid Benzenepropionic acid Benzylacetic acid Dihydrocinnamic acid Phenylpropanoic acid 3-Phenylpropanoic acid Phenylpropionic acid 3-Phenylpropionic acid P-Phenylpropionic acid... 

Dynamic resolution reactions couple the in situ racemization of a starting material with a kinetic resolution, thereby providing a route for the conversion of both enantiomers of starting material into one enantiomer of product. However, there is an important caveat the reaction product must be essentially inert to racemization. In control studies, 2-phenylpropionic acid (224 R = H) has been shown to racemize only slowly when treated with DABCO (l,4-diazobicyclo[2.2.2]octane) in water-DMSO (1 19) at 40 °C, whereas its phenyl ester (224 R = Ph) treated similarly was almost completely racemized in 7h. This work led to a procedure employing Candida cylindracea lipase (CCL) in which D,L-2-phenylpropanoic acid underwent a promisingly efficient dynamic kinetic resolution (Scheme 40). ... 

Figure 16.2-47. Resolution of racemic (R,S)-2-phenylpropionic alcohol with whole cells of Gluconobacter oxydans yielding (S)-2-phenylpropanoic acid and (R)-2-phenylpropionic alcohol.

In 1993, a perfluorocarbon was used as a reaction solvent for azeotropic transesterification reactions of carboxylic acid esters. One of the ultimate goals of transesterification is the use of a 1 1 ratio of ester and alcohol. Such a 1 1 transesterification was recently achieved using a fluorous version of the Otera method, which is based on tetraalkyldistannoxane. For example, octanol and ethyl 3-phenylpropionate were added to an FC-72 solution containing fluorous stannoxane [(C6Fi3CH2CH2)2SnO] 15. The mixture was then sealed and heated at 150°C for 16h. When the mixture was cooled, phase separation occurred and octyl 3-phenylpropanoate was obtained by separation and evaporation of the upper layer (Scheme 19). The lower FC-72 layer, which contained the catalyst, was used more than 20 times without any loss in catalytic activity. ... 

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