Ethyl hydrocinnamate

With cobalt catalysts, hydroformylation of ethyl cinnamate gave 91% of the hydrogenation product ethyl hydrocinnamate (15) and only 8% of the expected lactone, 16 (72). However, rhodium catalysis was effective in directing the reaction in favor of hydroformylation (70). The comparative results obtained with cobalt and rhodium are outlined in Table XXV. 

Chen et al.[57] reported the synthesis of the 2-hydroxyethylene isostere using two methods. The first method is initiated with readily available a-amino acids and utilizes the Evans chiral aldol condensation to control the stereochemistry (Scheme 25). The second method does not start with a-amino acids, and thus allows for the synthesis of isosteres having side chains other than those obtained from the available a-amino acids (Scheme 26). Thus, this synthesis relies on an anti-aldol product for the 2-hydroxyethylene isosteres via an E-selective ethyl hydrocinnamate enolization. 

Methyl hydrocinnamate Ethyl hydrocinnamate Propyl hydrocinnamate Butyl hydrocinnamate... 

Ethyl hydrate. See Alcohol Ethyl hydride. See Ethane Ethyl hydrocinnamate. See Ethyl-3-phenylpropionate... 

Phenylpropanoic acid ethyl ester (ethyl hydrocinnamate)... 

Na added all at once with vigorous stirring and some initial cooling to a mixture of ethyl hydrocinnamate, ethanol, phenol, and some quinoline, heated in an oil bath at 150°, then the temp, raised to 170° until the Na has disappeared after 15 min. phenylpropyl alcohol. Y 90%.—Similarly at 170-230° Ethyl L-leucinate —leucinol. Y 67%.—This method gives higher yields of amino-alcohols from amino esters with unprotected amino groups than the original Bouveault-Blanc procedure. F. e., also without addition of quinoline, s. W. Enz,. Helv. U, 206 (1961). 

The ketones are readily prepared, for example, acetophenone from benzene, acetyl chloride (or acetic anhydride) and aluminium chloride by the Friedel and Crafts reaction ethyl benzyl ketones by passing a mixture of phenylacetic acid and propionic acid over thoria at 450° and n-propyl- p-phenylethylketone by circulating a mixture of hydrocinnamic acid and n-butyric acid over thoria (for further details, see under Aromatic Ketones, Sections IV,136, IV,137 and IV,141). 

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 ... 

Ethyl p-phenylethyl ketone. Use 100 g. of pure hydrocinnamic acid and 200 g. (201 -5 ml.) of pure propionic acid. Fractionation of the distillate yields 70 g. of diethyl ketone (b.p. 100-102°), 72 g. of ethyl p-phenyl-ethyl ketone (b.p. 245-249° the pure ketone boils at 248°), and 18 g, of crude di-p-phenylethyl ketone (high b.p. residue). 

Interposition of a methylene group between the phenyl ring and the heterocycle leads to the benzyldiami nopyrimidines, a class of compounds notable for their antibacterial activity. Condensation of hydrocinnamate 54 with ethyl formate leads to the hydroxymethylene derivative 55. In this case, too, the heterocyclic ring is formed by reaction with guanidine. This sequence probably involves initial addition-elimination to the forniyl carbon to form 56 cyclization in this case involves simple amide formation. Tautomerization then affords the hydroxy derivative 57. This is converted to tetroxoprim (58) by first... 

Benzylacetophenone has been prepared by the reduction of benzalacetophenone with zinc and acetic acid1 and catalytic-ally with palladium and hydrogen 2 by the reduction of /3-duplo-benzylidene acetophenone monosulfide 3 by the oxidation of the corresponding car bind with chromic acid 4 by the hydrolysis of ethyl benzyl benzoylacetate 5 from acetophenone and benzyl chloride by the action of sodamide 6 and from benzoic and hydrocinnamic adds using as catalysts manganese oxide 7 and ferric oxide.8... 

Hydrocinnamic acid Aliphatic acid (3-Phenyl ethyl alkyl ketone... 

Hydrocinnamic acid, a-acetyl-2,3-dimethoxy-, ethyl ester)... 

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