Phenylpropenoic acid

In the context of preparing benzothienyloxy phenylpropanamines as inhibitors of serotonin and norepinephrine uptake, a group from Eli Lilly and Company has developed a two-step synthesis of benzo[fo]thiophenes (Scheme 6.193) [354]. Thus, a 2-mercapto-3-phenylpropenoic acid derivative was cyclized with iodine in 1,2-dimethoxyethane at 120 °C to give 5-fluoro-4-methoxybenzothiophene-2-carboxylic acid in 67% yield. Decarboxylation under strongly basic conditions involving 1,8-di-azabicyclo[5.4.0]undec-7-ene (DBU) as base in N,N-dimethylacetamide (DMA) as... 

Chiral catalysis was introduced in industrial synthesis in the mid-1970 s. The standard example is the catalytic hydrogenation of dehydroamino acid derivatives such as (Z)-2-acetyl-amino-3-phenylpropenoic acid with chiral rhodium complexes to give /V-acetylphenylalanine in high optical purity1. 

Problem 17.45 Prepare 3-phenylpropenoic acid from maionic ester and C H,CH.Br. 

Exercise 18-47 Explain why the Michael addition of diethyl propanedioate to 3-phenylpropenoic acid is unlikely to be successful. 

Zs-3-Phenylpropenoic acid (0.025 g, 0.16 mmol), Amberlite IRA 938-supported formate (0.2 g) and Wilkinson s catalyst (0.04 g, 0.0043 mmol) were suspended in dimethylsulfoxide (0.5 ml) in a reaction tube. The mixture was irradiated with microwaves at 100 W for 30 s. On cooling, the mixture was diluted with dichloromethane (5 ml) and filtered. The filtrate was washed with water (2x5 ml). The organic layer was dried over anhydrous magnesium sulfate, the solvent removed under reduced pressure, and the residue was purified by filtration through a plug of alumina to give 3-phenylpropanoic acid (0.024 g, 95% yield). 

What products are obtained from the bromination of cinnamic acid [(E)-3-phenylpropenoic acid] Draw the structural formulae of the products as Fischer projection formulae. What relationship do the products have to one another ... 

Peroxide Value (Appendix VII), 108 L-Phenylalanine, 5 3-Phenylpropenoic Acid, 66 Phospholipase A2, 18 Phytase (Aspergillus niger var.), 20... 

Problem 17.36 Prepare 3-phenylpropenoic acid from malonic ester and C6H5CH2Br. 

PHENYLPROPENOIC ACID see CMP975 3-PHENYL-2-PROPENOIC ACID see CMP975 3-PHENYL-2-PROPENOIC ACID METHYL ESTER (9CI) see MI0500... 

In the Perkin reaction, the carbanion is generated by abstraction of an a-hydrogen from an acid anhydride, with the anion of the corresponding acid acting as the base. For example, reaction of benzaldehyde with acetic anhydride in the presence of sodium acetate at high temperature yields 3-phenylpropenoic acid (Scheme 6.22). Although the mech-... 

FEMA No. 2288 Kyselina skoricove NSC 9189 Phenylxrylic acid 3-PhBnylxrylic acid 3-Phenylpropenoic acid 3-Phenyl-2-propenoic xid 2-Propenoic xid, 3-phenyl- Zimtsaeure Zimtsaure. A chemical intermediate used in perfumes and as an anthelmintic. Monoolinio crystals mp = 133° bp n 300° Am = 273 nm (EtOH) soluble in H2O (0,5 g/l), more soluble in organic solvents. Aceto Corp. Degussa-Huls Corp. Penta Mfg. Raschig GmbH. 

The alternative addition mechanism, introduced briefly in the paragraph immediately preceding, seems to have arisen from observations on the comparative behaviour of propenoic and 3-phenylpropenoic acids towards dialkyl chlorophosphites, (RO)2PCf and involves attack on the protonated ester molecule by the acid anion, a sequence which liberates the dialkyl hydrogenphosphonate (and isolated in some experiments ) and alkyl propenoate (Scheme 42) the overall reaction sequence is then terminated by the addition of dialkyl hydrogenphosphonate to the alkyl propenoate to give the observed product. 

Synonyms CAS 621-82-9 PHENYLACRYLIC acid tert-p-PHENYLACRYLIC acid 3-PHENYLACRYLIC ACID 3-PHENYLPROPENOIC ACID 3-PHENYL-2-PROPENOIC ACID... 

Synonyms Cinnamylic acid 3-Phenylacrylic acid p-Phenylacrylic acid t-P-Phenylacrylic acid 3-Phenylpropenoic acid 3-Phenyl-2-propenoic acid Empincal C9H8O2 Formula CeHsCHiCHCOOH Properties Wh. monoclinic cryst., honey floral odor sol. in benzene, ether, acetone, glac. acetic acid, carbon disulfide, fixed oils m.w. 148.17 dens. 1.2475 (4/4 C) m.p. 133 C b.p. 300 C flash pt. > 212 F... 

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