3-phenylpropanoyl acid chloride

The cyclization of 3-phenylpropanoyl acid chloride to 1-indanone can be performed in boiling benzene with 90% yield. The in situ formation of mixed carboxylic-fluorosulfonic anhydride intermediates is suggested to account for the high catalytic activity of Nafion. 

The ketocarbene is formed from 3-phenylpropanoyl chloride (dihydrocinnamic acid chloride) and diazomethane ring substituted dihydrocinnamic acids provide a route to substituted azulenes. Alternatively the keto group in (25) may be treated with a Grignard reagent for the introduction of alkyl substituents into the five-membered ring. 

Monodirectional 12 membered ring zeolites (offretite, L, mordenite and 0) are very inefficient as catalysts for formaldehyde benzene condensation to give diphenylmethane, esterification of phenylacetio acid with equimolar amounts of ethanol, Friedel-Crafts acylation of 3-phenylpropanoyl chloride with anisole and Claisen-Schmidt condensation of acetophenone with benzaldehyde. This fact has been attributed to diffusional constraints of organic compounds inside the channels. By contrast, the behaviour of the tridireotional f zeolite is very similar to that of dealuminated HY zeolites, inoreasing the turnover of the acid sites with the framework Si-to-Al ratio. 

In the present paper we have studied four acid catalyzed reaotions involving carbonyl compounds alkylation of benzene with formaldehyde, esterification of phenylacetic acid, Friedel-Crafts acylation by phenylpropanoyl chloride, and the cross aldolic condensation of acetophenone with benzaldehyde in the presence of three Hp zeolites with different framework Si-to-Al... 

Friedel-Crafts acylation of 3-phenylpropanoyl chloride (0.59 mmol) in anisole (50 ml) at 408 K in the presence of acid zeolites (1,00 g) for 17 h of reaction time. 

Secondly, the product distribution for the reaction of 3-phenylpropanoyl chloride with anisole catalyzed by zeolite beta (Table 4) is very similar to that found for acid faujasites and quite different to the AICI3 catalysis in which the ratio of 3 to 4 obtained is 7.0. Taking into account the adsorption properties of zeolites, their enhancement of the intermolecular reaction could be attributed to a high concentration of both reagents inside the cavities, thus promoting more efficiently the formation of the propiophenone 4 than a conventional AICI3 catalyst. 

Currently, the most widely practised procedure for the quantitative estimation of diastereoisomeric purity (d.e.) and thus of enantiomeric purity (e.e.) consists in the derivatization of the aminoalkyl phosphonic acid as the A-(3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl) derivative the latter is prepared from (R)-(+)-(3,3,3-trifluoro-2-methoxy-2-phenyl)propanoyl chloride (the so-called Mosher reagent) Although the diastereoisomeric derivatives 123 may also be separable by HPLC (e.g. on Zorbax-Sil) and which can be separately characterized [the derivative from (+)-Val was shown by X-ray... 

The submitters have found the iV-bromosuccinimide procedure to be a very general reaction. Alkyl, alicyolio, aryl and heterocyclic acetic acids have been brominated in 50-80% yield. The reaction may be applied in the presence of labile benzylic hydrogens for example, 3-phenyl-propanoic acid gives exclusively the 2-bromo-3-phenylpropanoyl chloride. The procedure has several significant advantages it is considerably faster than the known methods (overall reaction times of 2 hours are common), the use of bromine is circumvented, and work-up is considerably simplified. 

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