Benzaldehyde sulphonates

Kozinenko and Shilov studied the kinetics of oxidation of the o-, m-, and p-benzaldehyde sulphonate ions. In buffered solutions of pH 4-13 the rate equation is 

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From toluene suspended in dilute sulphuric acid (density 1 22) it is possible to obtain benzaldehyde and benzoic acid if A.C. be superimposed upon D.C., whereas with D.C. only, the toluene is completely oxidised to carbon dioxide and water. Similarly p-benzaldehyde sulphonic acid is obtained from toluene sulphonic acid. 

Allan FJ, Allan GG, Crank G, Jack J. The condensation of rhodanine and derivatives with benzaldehyde sulphonic acids. Red. Trav. Chim. Pays-Bas. 1960, 79, 247-254. 

Hydrolysis of the diethylacetal function employing p-toluenesulphonic acid in acetone, pyridinium p-toluene-sulphonate in EtOH, and a suspension of Si02 in hexane. In all cases the corresponding aldehyde is obtained in high yield as a Z E isomeric mixture. Transmetallation of acetal with Me2Cu(CN)Li2 followed by treatment with c-hexenones giving the 1,4-addition product. Alternatively, transmetallation with n-BuLi and reaction with benzaldehyde giving the expected alcohol. 

Benzaldehyde-2-sulphonic acid sodium salt [1008-72-6] M 208.2. Forms prisms or plates by extracting with boiling EtOH, filtering, evaporate to dryness and recrystallise the Na salt from a small volume of H2O. The N-phenylhydrazone sodium salt recrysts from H2O, m 174.5°. [A 299 363 1898]. 

Substituted aldehydes and substituted amines also react for example, the sodium salt of a-naphthylamine 4-sulphonic acid when dissolved in water and shaken with an alcoholic solution of benzaldehyde yields sodium benzylidine naphthionate. 

When the barium salt is treated with an aldehyde, c.y. salieylaldehyde or benzaldehyde, barium hydroxybenzylidenehydrazinomonosulphonate, (OH.CsH4.CH N.NH.S03)2Ba.2H20, and barium benzylixienehydrazinomonosulphonale, (CH.C H5 N. NH. S03) 2Ba.2H20, were formed. If ethylenediamine be sulphonated like hydrazine, barium ethyknediamino-monosulphonate, (NH2.CH2.CH2.NH.S03)2Ba, is formed and when this is treated for the free acid, there are formed colourless leaflets of ethylmediaminomonosulphomc acid, NHj.CHj.CHj.NH.HSO.,. or... 

This sequence serves to exemplify the formation and aspects of reactivity of toluene-p-sulphonate esters in monosaccharide systems, and further to illustrate the selective protection afforded to hydroxyl groups by the formation of cyclic acetals by reaction with carbonyl compounds. Thus reaction of methyl a-D-glucopyranoside (26) with benzaldehyde in the presence of zinc chloride gives the 4,6-acetal (27) (Expt 5.118), wherein two fused six-membered rings of the frans-decalin type are present. As a cognate preparation the reaction of benzaldehyde with methyl a-D-galactopyranoside results in a similar conversion to a 4,6-acetal, but in this case the product is the conformationally flexible system of the cis-decalin type, the most likely conformation being that shown below. 

Forbes and co-workers9 have extensively studied the ultra-violet absorption spectra of several series of disubstituted benzene derivatives acetophenones, benzoic adds, benzaldehydes, phenylbenzoates, acetanilides- nitrobenzenes, anilines, fluorobenzenes, chlorobenzenes, phenols and anisoles. They have collected valuable data and interpreted them in terms of the resonance and steric interactions of substituents. Baliab. and co-workers27 have studied the absorption spectra of aryl sulphones and sulphoxides. The absorption spectra of substituted phenylazides28 and phenyl isothiocyanates29 have been discussed by Rao et al. 

Phenol chromium tricarbonyl complex, n-butyllithium (2,mols) tertramethylethylenediamine (3 mols.) in THF at 60C for 3h. Benzaldehyde added and after oxidative decomplexation by addn. of Ij and camphor sulphonic acid in 10%HC/THF l-(3-hydroxyphenyl)benzyl slcohol obtained. 

Sulphone, 202 o-Fluobenzoio acid, 127 m-Fluobenzoic acid, 124 p-Fluobenzoic acid, 186 o-Chlorobenzoic acid, 141 m-Chlorobenzoic acid, 158 p-Chlorobenzoic acid, 242 o-Bromobenzoic acid, 148 m-Bromobenzoic acid, 155 p-Bromobenzoic acid, 251 o-Iodobenzoic acid, 162 m-Todobenzoic acid, 186 p-Iodobenzoic acid, 269 S Benzyl-wo-thiuronium picrate, 188 Benzaldehyde plienyl-hydrazone, 156 Benzoic acid, 121... 

Similarly, the commercial resins Wofatit K and Wofatit K.S. marketed by I. G. Farben are made by reacting benzaldehyde-2 4-di-sulphonic acid, resorcinol and formaldehyde. Phenol is also present in the production of Wofatit K.S. The final heating stage with formaldehyde is continued until a gel is formed. This is then cooled, washed and dried for several days at 80°C to 90°C, to give a resin which is fairly hard and has an exchange capacity of about 2-8 m-eq/g. ... 

Mix and stir the benzaldehyde resin (1 g, 0.59 mmol) with anhydrous ethylene glycol dimethyl ether (10 ml), glycol (1 g), and p-toluene-sulphonic acid (10 mg) for 24 h at 90°C. 

Meta substituted products are also obtained in the case of benzoic acid, benzaldehyde and benzene sulphonic acid. 

Cl5H15N3O2, p-Nitrobenzylidene-p dimethylaminoaniline, 42B, 84 Cl5H1gNjOftS, p-Dimethylaminobenzyl-p-nitrophenyl-sulphone, 44B, 100 Cl 5H1 7C1Ni,02, p-Dimethylamino-benzaldehyde-p-nitrophenylhydrazone hydrochloride, 42B, 46... 

The 4, 6 -Q-benzylidenated p-nitrophenyl a-maltopentaoside has been prepared using benzaldehyde dimethylacetal and toluene-p-sulphonic... 

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