Benzaldehyde, by condensation

Benzaldehyde, by condensation of phenyllithium with 1,1,3,3-tetra-methylbutyl isonitrile, 51,38 by reduction of benzonitrile with Raney nickel alloy, 51,22 BENZALDEHYDE, 3,4,5-TRIMETH-OXY-, 51,8... 

Cinnamic Acid by Perkin s Reaction.—Cinnamic acid has the constitution assigned to it above as is proven by the following synthesis from benzaldehyde by condensation with sodium acetate in the presence of acetic anhydride. 

Mandellic Acid.—Mandellic acid is phenyl glycolic acid, CeHs— CH(OH)—COOH, phenyl hydroxy acetic acid. This constitution is proven by its synthesis from benzaldehyde by condensation with hydrogen cyanide and the hydrolysis of the resulting nitrile. 

Atophan (or cihchophen) may be prepared by condensing equimolecular proportions of benzaldehyde, aniline and pyruvic acid in alcoholic solution ... 

By condensing carbon oxysulfide with o-aminOnitriles the corresponding 2-hydroxy-5-aminothiazoles can be obtained. In the presence of benzaldehyde or its substituted derivatives the reaction leads to 5-benzy-lideneaminothiazole derivatives (218) in good yields (Scheme 114 and Table 11.35) (393, 442). However, the reaction fails with or-amino acetonitrile (206), R = H (317). The 2-alkoxy analogs (220), R = Me, Et, Pr, Bu, vinyl, were similarly obtained from 219 and benzylideneamino acetonitrile (Scheme 115a) (393). 

Reactions were carried out by condensing the o-aminoacetonitrile with carbon oxysulfide in the presence of benzaldehyde or its substituted derivatives, in aicoho) as solvent. 

Benzylacetone, [2550-26-7] CgH CH2CH2COCH2 (bp, 233—234°C at 101.3 kPa) is produced by condensing acetone and benzaldehyde, followed by selective hydrogenation, and is used in soap perfumes. 

Syntheses of members of the lobeline group have been effected by Wieland and Drishaus and by Seheuing and Winterhalder. JiorLobelane was prepared by the former authors by condensing 2 6-dimethylpyridine with benzaldehyde to 2 6-distyrylpyridine (IX), which was then reduced by sodium in alcohol, giving a mixture of meso-and trans- forms of 2 6-di-(3-phenylethylpiperidine (worlobelane). From this by crystallisation of the mixed hydrochlorides, meso-norlobelane was separated, which on A-methylation yielded lobelane (X) as the methiodide. 

Activity is apparently retained when the ring nitrogen is alkylated as in flordipine (42). Aldol condensation of the benzaldehyde 39 with ethyl acetoacetate gives the unsaturated ester 40. The nitrogen containing reaction partner 41 is obtained by condensation of 32 with 2- morpholi-noethylamine. Reaction of 40 with 41 leads to flordipine (42) [12]. 

Microwave and fluorous technologies have been combined in the solution phase parallel synthesis of 3-aminoimidazo[l,2-a]pyridines and -pyrazines [63]. The three-component condensation of a perfluorooctane-sulfonyl (Rfs = CgFiy) substituted benzaldehyde by microwave irradiation in a single-mode instrument at 150 °C for 10 min in CH2CI2 - MeOH in the presence of Sc(OTf)3 gave the imidazo-annulated heterocycles that could be purified by fluorous solid phase extraction (Scheme 9). Subsequent Pd-catalyzed cross-coupling reactions of the fluorous sulfonates with arylboronic acids or thiols gave biaryls or aryl sulfides, respectively, albeit it in relatively low yields. 

The 3-arylglutaric esters 3 required as substrates were obtained by condensation of 2 equiv. of ethyl acetylacetate with respective benzaldehydes, followed by hydrolysis and decarboxylation of the resulting product under basic conditions. After esterification, ester 3 was obtained in 75% overall yield (R = Cl, = Me) [10]. 

Aldol condensation reactions have also been conducted. A good example is provided by Climent et al. (1998) for making a-n-amyl cinnamaldehyde (Jasmin aldehyde) by condensing benzaldehyde with n-heptaldehyde, in the presence of mesoporous MCM-41 aluminosilicates. Mesoporous silica-aluminas with a narrow range of pore diameter such as MCM-41 also... 

Uncharged styryl (methine) disperse dyes were originally introduced to provide greenish yellow colours on cellulose acetate fibres. One such dye still in use is Cl Disperse Yellow 31 (6.226), which is made by condensing 4-(N-butyl-N-chloroethylamino)benzaldehyde with ethyl cyanoacetate. Suitable compounds for polyester usually contain the electron-accepting dicyanovinyl group, introduced with the aid of malononitrile. An increased molecular size leads to improved fastness to sublimation, as in the case of Cl Disperse Yellow 99 (6.227). A novel polymethine-type structure of great interest is present in Cl Disperse Blue 354 (6.228), which is claimed to be the most brilliant blue disperse dye currently available [85]. 

A similar approach was used to prepare the octaglucosylated porphyrin derivative 34a obtained quantitatively after treatment of 34b with sodium methoxide and dry methanol (Fig. 3). The aldehyde used in the preparation of octaglucosylated derivative 34b was obtained in 90% yield by condensation of 3,5-dihydroxybenzaldehyde with acetobromoglucose 30 in the presence of Ag20.22 The condensation of pyrrole and the 2,5-bis(tetra-acetylglucopyranosyloxy)benzaldehyde occurred under Lindsey conditions and yielded porphyrinylsugar derivative 34b in 32%.22... 

It is obtained by condensing benzaldehyde-o-sulfonic acid with 2 equivalents of N-ethylbenzylaniline, followed by sulfonation, oxidation, and conversion to the ammonium salt. The dissolved dye is then immersed in a dispersion of aluminum hydroxide and converted to the corresponding salt using aluminum chloride or barium chloride solution ... 

Ephedrine Ephedrine, L-erythro-l-phenyl-2-methylaminopropanol-l (11.3.4), is synthesized from benzaldehyde in a few different ways. According to the first, benzaldehyde is condensed with nitroethane, giving 2-methyl-2-nitro-l-phenylethanol (11.3.2), which is reduced to 2-methyl-2-amino-l-phenylethanol (11.3.3). The necessary L-isomer is isolated from the mixture of isomers by crystallization. Methylation of this gives ephedrine (11.3.4) [52,53]. 

Tripelennamine Tripelennamine, iV-benzyl-iV, Ai -dimethyl-iV-2-pyridylethylenediamine (16.1.6), is synthesized by reacting 2-benzylaminopyrridine (16.1.5) with 2-dimethy-laminoethylchloride in the presence of sodium amide. 2-Benzylaminopyrridine, in turn, can be easily synthesized by reduction of a Schiff base, synthesized by condensation of 2-aminopyrridine with benzaldehyde [9-11]. 

By subsequent hydrolysis phenylalanine and phenylacetic acid result. The proof of this reaction was given by the synthesis of phenylacetyl-phenylalanine by condensing benzaldehyde with phenaceturic acid —... 

A number of syntheses of pioglitazone have been disclosed (Arita and Mizuno, 1992 Fischer et al., 2005 Les et al., 2004 Meguro and Fujita, 1986, 1987 Momose et al., 1991 Prous and Castaner, 1990 Saito et al., 1998). Two related syntheses (Fischer et al., 2005 Les et al., 2004) of pioglitazone hydrochloride are described in Scheme 8.2. The tosylate of 2-(5-ethylpyridin-2-yl)ethanol (16), formed in situ with tosyl chloride, was displaced by 4-hydroxybenzaldehyde (17) by means of benzyltributylammonium chloride and NaOH to give 4-[2-(5-ethylpyridin-2-yl)ethoxy]benzaldehyde (20). Condensation of 20 with thiazolidine-2,4-dione in basic medium afforded 5-[-4-[2-(5-ethylpyridin-2-yl)ethoxy]benzylidene]thiazolidine-2,4-dione (21). Finally, this compound was hydrogenated to provide pioglitazone (2). Alternatively, a nucleophilic aromatic substitution reaction... 

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