Hydrocinnamic acid, /3-methyl

The dibenzyl ketone has a very high b.p. (ca. 200°/21 mm.) and this remains in the flask when the unsymmetrical ketone has been removed by distillation. The dialkyl ketone has a comparatively low b.p. and is therefore easily removed by fractionation under normal pressure acetone is most simply separated by washing with water. In this way methyl benzyl ketone (R = CHj), ethyl benzyl ketone (R = CHgCH,) and n-propyl benzyl ketone (R = CHjCHjCH,) are prepared. By using hydrocinnamic acid in place of phenylacetic acid ... 

Methyl Phenyl-propionate,—Phenyl-propionic acid, also known as hydrocinnamic acid, forms a methyl ester of the formula... 

If undiluted methyl alcohol is used as a solvent a secondary catalytic action of the palladium results in the production of ester.1 In this case 5 g. of potassium hydroxide are added, the solution is concentrated by heating, and hydrocinnamic acid precipitated with dilute hydrochloric acid. 

Using the same procedure the following ketones may be obtained in similar yields ethyl benzyl ketone from phenylacetic acid and propionic acid, methyl 8-phenylethyl ketone from hydrocinnamic acid and acetic acid, and ethyl /3-phenylethyl ketone from hydrocinnamic acid and propionic acid. 

C13H15N02 (3R-cis)-7a-methyl-3-phenyltetrahydropyrrolo 137869-70-6 25.00 1.1104 2 26214 C13H1802 a-(tert-butyl)hydrocinnamic acid 53483-12-8 23.75 0.9943 2... 

Methyls are trans in NN, PP cis in OO, QQ, RR (b) NN is resolvable. 22. See p. 1087. 23. (a) Ethyl acetate (b) methacrylic acid (c) phenylacetamide. 24. (a) /i-Propyl formate (b) methyl propionate (c) ethyl acetate. 25. SS, benzyl acetate TT, methyl phenylacetate UU, hydrocinnamic acid, PhCH2CH2COOH. 26. Ethyl anisate. 27. VV, vinyl acetate. 28. (a) Ethyl adipate (b) ethyl ethylphenylmalonate ethyl aoet-amidomalonate. 

The large scale preparation of (S)-2 [(tert-butylsulfonyl)-methyl]hydrocinnamic acid [(S)-4], a chiral building block in the synthesis of the potential rennin inhibitor Remikiren (not in use since it failed in the clinical phase), was performed via Subtilisin Carlsberg-catalyzed racemic resolution of the ester roc-3. The substrate was emulsified at 39-43 °C in 29% concentration in aqueous buffer and the pH was controlled using a 2-4 M NaOH solution. Work-up proved to be the rate-limiting step, nevertheless, the desired product could be isolated in 41.6% yield on a 100 kg scale. The product was obtained with excellent chemical (>99.5%) and enantiomeric (>99%) purity (Scheme 4.8). 

B. Wirz, S. Doswald, E. Kupfer, W. Wostl, T. Weisbrod, H. Estermann, Protease-Catalyzed Preparation of (S)-2-[(tert-butylsulfonyl)-methyl]-hydrocinnamic Acid for Rennin Inhibitor RO0425892, in H.-U. Blaser, E. Schmidt (Eds.), Asymmetric Catalysis on Industrial Scale, Wiley-VCH, Weinheim, 2004, pp. 385-398. 

Protease-Catalyzed Preparation of (S)-2-[(tert-Butylsulfonyl)methyl]-hydrocinnamic Acid... 

Hydrocinnamic acid, 3,5-di-t-butyl-4-hydroxy-, methyl ester. Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, methyl ester EINECS 228-985-4 Hydro-cinnamic acid, 3,5-di-t-butyl-4-hydroxy-, methyl ester Methyl 3-(3,5-di-t-butyl-4-hydroxyphenyljpropionate,... 

Hydrocinnamic acid 2-[2-Hydroxy-3,5-di-(1,1-dimethylbenzyl) phenyl]-2H-benzotriazole Lithium iodide Magnesium salicylate 2,2 -M ethylenebis (6-t-butyl-4-methyl phenol) 4,4 -Methylenebis (2,6-di-t-butylphenol) 2,2 -Methylenebis (4,6-di-t-butylphenyl) 2-ethylhexyl phosphite 2,2 -Methylenebis (4-ethyl-6-t-butylphenol) 2,2 -Methylenebis (4-methyl-6-t-butylphenol) monoacrylate 2,2 -Methylenebis 6-h -methylcyclohexyl)-p-cresol 2,2, 2"-Nitrilo [triethyl-tris (3,3, 5,5 -tetra-t-butyl-1,1 -biphenyl-2,2 -diyl) phosphite] ... 

Hexyl 2-methyl butyrate Hexyl octanoate Hexyl phenylacetate Hexyl propionate Hydrocinnamaldehyde Hydrocinnamic acid Hydrocinnamic alcohol Hydrocinnamyl acetate Hydrogen sulfide p-Hydroxybenzaldehyde... 

Amino-6-ethoxybenzothiazole C9HioN402S2 Sulfamethizole C9H10O 2-Ally I phenol Cinnamyl alcohol 2,4-Di methyl benzal dehyde p-Ethylbenzaldehyde Ethyl phenyl ketone Hydrocinnamaldehyde 4 -Methyl acetophenone 2-Phenyl propanal Propiophenone p-Tolylacetaldehyde C9H10O2 Acetanisole Benzyl acetate m-Cresyl acetate o-Cresyl acetate p-Cresyl acetate p-Ethoxybenzaldehyde Ethyl benzoate Hydrocinnamic acid 2-M ethoxy-4-vi nyl phenol a-Methylbenzyl formate Methyl phenylacetate Methyl p-toluate Phenethyl formate Phenyl glycidyl ether... 

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