Phenyl crotonic acid

The hydiobiomides of /3-y unsaturated acids like /S-phenyl-crotonic acid beha e Cjuite differently. On l oiling with water, lactones are formed, i.e., inner anhydrides of o. y-acids,... 

Phenyl Crotonic Acid. Phenyl Vinyl Acetic Acid.—A phenyl derivative of crotonic acid is known, CeHs—CH2—CH = CH—COOH, beta-benzyl acrylic add. Also the structural isomer of crotonic acid, viz., vinyl acetic acid, CH2 = CH—CH2—COOH, yields a phenyl derivative, CeHs—CH=CH—CH2—COOH, phenyl vinyl acetic acid or I-phenyl Ai-butenoic-4 acid, which is important in connection with the constitution of naphthalene (p. 768). 

An ethereal soln. of diethylamine added to an ethereal soln. of methyl 3-hydroxy-3-phenyl-l-propyne-l-carboxylate at 0°, and allowed to stand overnight at the same temp. —> -diethylamino-y-hydroxy-y-phenyl crotonic acid lactone. Y 70% (cf. Synth. Meth. 5, 57). (A. W. Nineham and R. A. Raphael, Soc. 1949, 118 also / -alkoxy derivatives s. E. R. H. Jones and M. C. Whiting, Soc. 1949, 1423.)... 

Actual dinocap Arathane 2-Butenoic acid, 2(or 4)-isooctyl-4,6(or 2,6)-dinitrophenyl ester 2-Butenoic acid 2-(1-methylheptyl)-4,5-dinitrophenyi ester Caprane Capryidinitrophenyl crotonate 2-Capryl-4,6-dinitro-phenyl crotonate Caratan Carathane Caswell No. 391D CR 1639 Crotonate de 2,4-dinitro 6-(1-methyl-heptyl)-phenyle Crotonic acid 2-(1-methylheptyl)-4,6-dinitro-phenyl ester Crotonic acid, 2(or 4)-(1-methylheptyl)-4,6(or 2,6)-dinitrophenyl ester Crotonic acid 2,4-dinitro-6-(2-octyl)phenyl ester Crotonic acid... 

Phenylpropyne-1 a-Methyl cinnamic acid -f a-phenyl crotonic acid 54 [345]... 

Carboxy-l-methylethyl)amino]-5-trifluoromethylaniline (120) gave 2-phenyl-7-trifluoromethylquinoxaline (122), probably by loss of crotonic acid and water from the unisolated intermediate (121) (neat BzCHO, 155°C, 3 h 82% note that no isomer was detected). " ... 

Chromium trioxide, 60, 21 Clemmensen reaction, 60, 111 Copper chloride (CuCl) [7758-89-6], 61, 122 Crotonic acid, ethyl ester, ( )-, 61, 85 18-Crown-6-potassium cyanide complex, 60,129 Crum Brown-Walker reaction, 60, 4 Cuprous chloride, 60, 42, 121 61, 122 CYANIC ACID, PHENYL ESTER [1122-85-6], 61, 35... 

Benzene may be alkylated by certain unsaturated, halo, hydroxy, and keto acids. The yields of phenyl-substituted acids are usually low (18-65%). In the alkylation of benzene by cinnamic and crotonic acids the major products are 3 phenyl- and 3-methyl-hydrindones, respectively, formed by subsequent ring closures by Friedel-Crafts acylation. ... 

Problem 27.7 Treatment of crotonic acid, CH CH—CHCOOH, with phenyl-hydrazine yields compound IV. 

Of the esters formed with unsaturated acids, the most important are 2-(l-methyl- -propyl)-4,6-dinitrophenyl-2-methyl crotonate (binapacryl, 10) and the product known under the name dinocap (II). which is a mixture of 2,4-dinitro-6-(2-isooctyOphenyl crotonate (11a) and 2,4-dinitro-4-(2-isooctyl)phenyl crotonate (11b) (Emmel and Czech, 1960). 

LLJ The ester of crotonic acid with (2-formyl)phenylethanol was treated with Li-tetramethyl-piperidide in a toluene/THF solution (10 1) in the presence of the Lewis acid Al-tris(2,6-di-phenyl)phenoxide at —48 °C for 1 h. After workup, a product A was isolated in 70% yield. 

CP 1309, see Pentachlorophenol CPD-244, see 2-Nittopropane CPD-926, see Dibenzofuran 4-CPPE, see 4-Chlorophenyl phenyl ether p-CPPE, see 4-Chlorophenyl phenyl ether Crag sevin, see Carbaryl Crawhaspol, see Trichloroethylene 2-Cresol, see 2-Methylphenol 4-Cresol, see 4-Methylphenol oCresol, see 2-Methylphenol p-Cresol, see 4-Methylphenol Crestoxo, see Toxaphene Crestoxo 90, see Toxaphene oCresylic acid, see 2-Methylphenol p-Cresylic acid, see 4-Methylphenol oCresyl phosphate, see Tri-ocresyl phosphate Crisalin, see Trifluralin Crisalina, see Trifluralin Crisfuran, see Carbofuran Crisulfan, see a-Endosulfan, p-Endosulfan Crisuron, see Diuron Crolean, see Acrolein Crop rider, see 2,4-D Crotenaldehyde, see Crotonaldehyde Crotilin, see 2,4-D Crotonal, see Crotonaldehyde Crotonic aldehyde, see Crotonaldehyde CRS, see Phenol Crunch, see Carbaryl Cryptogil OL, see Pentachlorophenol CS, see oChlorobenzylidenemalononitrile, Methyl mercaptan... 

A few drops of coned, sulfuric acid added to a mixture of ethyl acetoacetate and triethyl orthoformate, stored 24 hrs., and neutralized with a slight excess of quinoline ethyl j -ethoxy-cis-crotonate (Y 89%) dissolved in dry ether, added to a suspension of 2 moles LiNHg in anhydrous liq. NHg, stirring continued 10 min., a soln. of benzaldehyde in dry ether added, stirred 1 hr., NHg replaced by ether, refluxed 5 min., and ice-water added 3-ethoxy-5-phenyl-cis-2-frans-4-pentadienoic acid (Y 74%). — Excess LiNHg is used to prevent self-condensation of the ester. F. e. s. E. E. Smissman and A. N. Voldeng, J. Org. Ghem. 29, 3161 (1964). 

Methyl j -amino-a-(N-phenyl-p-methylbenzimidoyl)crotonate stirred ca. 30min. with 10 times its weight of polyphosphoric acid at 150-170° until effervescence ceases crude 3-acetyl-2-p-tolyl-4(lH)-quinoline. Y 70-90%. F. e. s. P. C. Anderson and B. Staskun, J. Org. Ghem. 30, 3033 (1965). 

Synonyms Ciodrin Ciovap Cyodrin Cypona E.C. 3-((Dimethoxyphosphinyl)oxy)-2-butenoic acid 1-phenylethyl ester (9,(9-Dimethyl (9-(l-methyl-2-carboxy-a-phenyl-ethyl)vinyl phosphate Decrotox Dimethyl-c/.s-l-methyl-2-(l-phenylethoxycarbo-nyl)vinyl phosphate Dimethyl phosphate of a-methylbenzyl 3-hydroxy-c/.s-crotonate Duo-kill Duravos ENT 24717 l-Methylbenzyl-3-(dimethoxyphosphinyloxo)isocroto-nate a-Methylbenzyl-3-(dimethoxyphosphinyloxy)-c/ -crotonate a-Methylbenzyl 3-hydroxycrotonate dimethyl phosphate Pantozol 1 c/.s-2-(l-Phenylethoxy)carbonyl-l-methylvinyl dimethyl phosphate SD 4294 Shell SD 4294 Volfazol. 

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