Methyl benzene sulfonate

Scrupulously dried base (0.5 g) in spectroscopically pure acetonitrile (B ml) was treated with methyl benzene sulfonate at room temperature for 22 hours. The filtered reaction mixture was added dropwise to mechanically stirred, filtered, dry ether (ca 450 ml). The flocculent white precipitate was filtered off, washed with dry ether, and dried in vacuo over P Os at 50°C to yield the product, an off-white powder melting at B5° to 90°C. 

A colleague of yours who investigates the fate of benzene sulfonates and benzene sulfonate esters in natural waters is interested in the stability of methyl-3,4-dichlorobenzene sulfonate (MDCBS) in aqueous solution. Because he has not read Chapter 13 of Environmental Organic Chemistry he asks you to help him to estimate the hydrolysis half-life of this compound in water at 25 °C and at 5°C. In the literature you find rate constants for the neutral hydrolysis of some substituted methyl benzene sulfonates at... 

The first representative of this class of meso-ionic heterocycles was the 1,3-dimethyl derivative (293, R1 = R2 = Me, R3 = H) obtained by methylation of 5-amino-2-methyltetrazole with methyl benzene-sulfonate.208 Meso-ionic l,2,3,4-tetrazol-5-acylimides (293, R1 = R2 = Me, R3 = Me.CO, p-Me.C6H4.S02, p-Cl.C5H4.SO2) have been prepared by methylation of the corresponding 1-methyltetrazole using dimethyl sulfate.209,210 The sequence 293, R1 = R2 = Me, R3 = Me.CO - R3 = H - R3 = p-Me.C6H4S02, was achieved by acid hydrolysis followed by tosylation. The substances (293, R1 = R2 =Me, R3 = H) prepared by the two routes are identical.208,210... 

Permanent Red 2B (Barium Red 2B, PR 48 1, Cl No. 15865 1 Calcium Red 2B, PR 48 2, Cl No. 15865 2 Manganese Red 2B, PR 48 4, Cl No. 15865 4). Discovered by DuPont in the early 1920s the permanent red 2B pigments are azo reds prepared from coupling diazotized l-amino-3-chloro-4-methyl benzene sulfonic acid onto 3-hydroxy-2-naphthoic acid (BON).The barium salt is characterized by a clean, yellow hue as compared to the bluer calcium salt. The barium salt has a poorer lightfastness and weaker tinting strength however the barium salt will provide better heat stability in certain polymer systems. The calcium salt provides the most widely used blue-shade red. 

After having been washed with 50 cc of water the benzene layer is dried over potassium carbonate, filtered, allowed to stand over 10 g of alumina for about VA hours for partial decolorization, filtered again and concentrated under reduced pressure. The oily base which remains as a residue is directly converted into the tartrate. A solution cooled to 0°C, of 6.50 g of the free base in 100 cc of acetic acid ethyl ester is thoroughly shaken and poured into an ice cold solution of 2.66 g of tartaric acid in 410 cc of acetic acid ethyl ester. The precipitated, analytically pure, tartrate of 3-methylsulfinyl-10-[2 -N-methyl-piperidyl-2")-ethyl-1 ]-phenothiazine melts at 115° to 120°C (foam formation) and sinters above B0°C. The base Is reacted with benzene sulfonic acid in a suitable solvent to give the besylate. 

FIGURE 15. The ( perpendicular ) torsional form of methyl-phenyl sulfone. The projection formula represents a view along the S—C(phenyl) bond. The other drawing shows the labels of the benzene ring angles. 

C7H802S, Methyl phenyl sulfone [(Methylsulfonyl)benzene]... 

V Disodium 4,4 -(2,4-diamino-5-methyl-l,3-phenylene-bisazo)di(benzene-sulfonate)... 

C8H10O2S, Benzyl methyl sulfone [(MethyIsulfonyl)methyl]benzene ... 

Rhodococcus sp. Strain T09 A Rhodococcus strain T09 was isolated by enrichment on media-containing BT. The desulfurization mechanism of this organism was reported to be similar to Gordonia sp. 213E due to the observation of similar intermediates however, the substrate specificity was different. The strain T09 could use 2-methyl, 3-methyl and 5-methyl BT apart from BT as sole source of sulfur for growth, but not 7-methyl or ethyl derivatives. Additionally, it could also use methyl thiobenzothiazole, marcaptobenzothiazole, as well as benzene sulfide, benzene sulfonate, biphenyl sulfinate, dimethyl sulfate, dimethyl sulfone, dimethyl sulfide, methane sulfonic acid, thiophene, and taurine as sole sulfur sources. However, it could not grow on DBT or DBT sulfone. 

Chemical Name 10-[2-(l-Methyl-2-piperidinyl)ethyl]-2-methylsulfinyl-10H-phenothiazine benzene sulfonate... 

After the mixture is cooled to 75°, 200 ml. of benzene is added (Note 5). The mixture is stirred briefly, and the liquid is decanted from the solid into a 5-1. separatory funnel. The aqueous layer is separated and extracted again with 200 ml. of benzene. The aqueous layer is then returned to the separatory funnel, and the solid in the reaction flask is washed in with it by means of 2 1. of water. The mixture is shaken with 200-ml. portions of benzene until all solid has dissolved (usually three portions of benzene suffice). All the benzene extracts are combined and dried with 20 g. of anhydrous calcium chloride. The drying agent is removed by filtration and washed with two 20-ml. portions of benzene. Benzene is removed from the filtrate by distillation under reduced pressure (Note 6), and the solid which separates is dried further at about 10 mm. and room temperature to constant weight. The yield (Note 2) of methyl -tolyl sulfone is 298-317 g. (69-73%), m.p. 83-87.5°. Further purification is generally unnecessary, but, if desired, the product may be recrystallized from carbon tetrachloride or ethanol-water (1 1). The submitters state that the method may be extended to the preparation of methyl phenyl sulfone and, presumably, of methyl aryl sulfones generally (Note 7). 

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