Of 3-benzoylpropionic acid

Perumal investigated a novel variation that involved the combination of a Vilsmeier reaction with a Paal-Knorr condensation. Reaction of 3-benzoylpropionic acid (87) under Vilsmeier conditions furnished chloroformylfuran 88 in 75% yield, while reaction of acetonylacetone (89) provided formylfuran 90 in 60% yield." ... 

Benzoylacrylic acid has been prepared by the condensation of acetophenone and chloral to l,l,l-trichloro-2-hydroxy-3-benz-oylpropane, followed by hydrolysis to the corresponding acid and dehydration by the action of iodine, potassium iodide, and sodium carbonate on 7-phenylisocrotonic acid by bromination of /3-benzoylpropionic acid and subsequent dehydrohalogena-tion 1 and by the action of phenylzinc chloride on maleic anhydride. The present method is based on the work of von Pech-mann and others. ... 

The preparation of the cyclic ketone a-tetralone possesses a number of interesting features. Succinic anhydride is condensed with pure benzene in the presence of anhydrous aluminium chloride (slightly over two equivalents see 1 above) to yield (3-benzoylpropionIc acid ... 

The oxidation of substituted /3-benzoylpropionic acids by PFC follows the Hammett relation with a negative reaction constant. A possible mechanism for the oxidation has been discussed.5 The oxidation of maleic, fumaric, crotonic, and cinnamic acids by PCC is of first order with respect to PCC and the acid. The oxidation rate in 19 organic solvents has been analysed by Kamlet s and Swain s multiparametric equations. A mechanism involving a three-centre transition state has been postulated.6 The relative reactivity of bishomoallylic tertiary alcohols toward PCC, to yield substituted THF products via the tethered chromate ester, is dependent only on the number of alkyl groups. This observation suggests a symmetrical transition state in this intramolecular Cr(VI)-alkene reaction.7 Mechanisms have been proposed for the oxidation of 2-nitrobenzaldehyde with PBC8 and of crotonaldehyde with tetraethylammonium chlorochromate.9... 

Catalytic hydrogenation over palladium-on-charcoal with perchloric acid promoter is more satisfactory than the Clemmensen method for the reduction of a-phenyl-/3-benzoylpropionic acid to a,y-diphenylbutyric acid (83%). Several other keto acids have been successfully hydrogenated over this catalyst. ... 

Benzoylpropionic acid has been prepared by the action of succinic anhydride on benzene in the presence of anhydrous... 

Isonitrosopropiophenone has been prepared from esters of a-benzoylpropionic acid by a process involving saponification, nitrosation, and decarboxylation 1 from phenylmethylglyoxal by the action of hydroxylamine 2 from propiophenone by treatment with amyl nitrite,3 methyl nitrite,4 or butyl nitrite. ... 

Many (benzo)pyridazines are made from 1,4-diketo compounds, and the industrial supply of, for example, maleic and phthalic anhydrides and mucohalic acids make them attractive and widely used starting materials, which can be used in conjunction with substituted hydrazines to give a range of A-substituted derivatives. Some other 1,4-diketo compounds are commercially available on a smaller scale, including, for example, certain 3-benzoylpropionic acids from which 6-aryl-4,5-dihydro-3(2//)-pyridazinones can be prepared. When such precursors are not commercially available then ease and scope of synthetic approaches to the starting materials must be considered, but for established routes, such as 6-aryl-4,5-dihydro-3(2//)-pyridazinones from 3-aroylpropionic acids, a variety of synthetic methods have been developed so that a wide range of (substituted)aroyl derivatives can be prepared. Synthetically useful preformed (benzo)pyridazine derivatives that are commercially available include 4,5-dichloro-3(2F/)-pyridazinone, 3,6-dichloropyridazine, and 1,4-dichlorophthalazine. 

The Al-chlorobenzamide (NCB) oxidized 3-benzoylpropionic acid (BRA) in AcOH-H2O-HCIO4 to the corresponding carboxylic acid. The reaction was first order in BRA, NCB, and H+ ion, and H2O+CI ion was the reactive species. Added benzamide decreased the rate, and lowering of the dielectric constant increased the rate. ... 

Preparation of N-Hydroxysuccinimide Esters. For the synthesis of the iV-hydroxysuccinimide esters of 3-(4-benzoylphenyl)propionic acid and 3-benzoyIpropionic acid, the method of Rappaport and Lapidot has been modified. 3-(4-Benzoylphenyl) propionic acid (765 mg, 3 mmoles) or 3-benzoylpropionic acid (534 mg, 3 mmoles) and Af-hydroxysuccinimide (345 mg, 3 mmoles) are suspended in dry ethyl acetate (6 ml) and cooled in ice. Dicyclohexylcarbodiimide (618 mg, 3 mmoles), dissolved in ethyl acetate (2 ml), is added under stirring. After 15 min in ice, the mixture is allowed to warm to room temperature and stirring is continued for 2 hr. Dicyclohexylurea is removed by filtration with suction and washed with ethyl acetate (20 ml). The combined filtrate is evaporated to dryness under reduced pressure (under 40°). The residue is crystallized from methanol. Yield 3-(4-benzoylphenyl)propionic acid A -hydroxysuccini-mide ester 810 mg (72%), m.p. 114°-115° 3-benzoylpropionic acid N-hydroxysuccinimide ester 540 mg (65%), m.p. 132°-134°. 

Preparation of S-Bemoylpropionyl-[ H]Phe-tRNA. [ H]Phe-tRNA (5 nmoles) is dissolved in 0.05 M potassium phosphate at pH 6.8 (0.1 ml) at 0°. 3-Benzoylpropionic acid iV-hydroxysuccinimide ester, 1 mg, dissolved in acetonitrile (0.05 ml) is then added, and the mixture is incubated for 5 hr at 37°. The tRNA derivative is precipitated with ethanol and stored dry at —20°. The degree of acylation is determined by thin-layer chromatography (Rf of 3-benzoylpropionylphenylalanine is 0.5) or by treatment with CUSO4 as described. The degree of acylation was usually about 95%. 

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