26908-82-7

Usage

Purification Methods

The most likely impurity is p-toluenesulfonic acid (could be up to 10%). This can be removed by dissolving it in dry Et2O and cooling until the anhydride crystallises out. It decomposes on heating; below ~130o it gives the disulfonic anhydride and above ~130o polymers are formed, but it can be distilled in a vacuum if it is free of acid. It is used for cleaving ethers [Prep, IR, NMR: Karger & Mazur J Org Chem 36 528, Karger & Mazur J Org Chem 36 532 1971]. [Beilstein 11 III 255.]

InChI:InChI=1/C9H10O4S/c1-7-3-5-9(6-4-7)14(11,12)13-8(2)10/h3-6H,1-2H3

Upstream product

• 16836-95-6 silver(I) 4-methylbenzenesulfonate 
• 75-36-5 acetyl chloride 
• 104-15-4 toluene-4-sulfonic acid 
• 127-09-3 sodium acetate 
• 98-59-9 p-toluenesulfonyl chloride 
• 108-24-7 acetic anhydride 
• 10534-59-5 tetrabutylammonium acetate 

Downstream Products

• 778-28-9 butyl para-toluenesulfonate 
• 103-84-4 Acetanilid 
• 147030-98-6 1-(4-phenylfuran-2-yl)ethanone 
• 61000-04-2 4,4'-Dimethoxy-β-methylchalcon 
• 108-21-4 Isopropyl acetate 
• 1118-69-0 N-isopropylacetamide 
• 1117-77-7 methyl N-acetylglycinate 
• 141-78-6 ethyl acetate 
• 599-91-7 propyl tosylate 
• 2307-69-9 toluene-4-sulfonic acid isopropyl ester 
• 34553-05-4 Acetic acid (Z)-4-(toluene-4-sulfonyloxy)-but-2-enyl ester 
• 26923-87-5 2-acetoxyethyl-2'-tosyloxyethyl ether 
• 19859-07-5 p-Toluolsulfonsaeure-(5-acetoxy-pentyl-2)-ester 
• 26923-85-3 Pentan-1,5-diolacetat-tosylat 

Relevant academic research and scientific papers

Correlation of the rates of solvolysis of acetic p-toluenesulfonic anhydride (acetyl p-toluenesulfonate) and a comparison with acetyl halides

The specific rates of solvolysis of acetyl p-toluenesulfonate have been measured by a rapid-response conductivity technique at temperatures in the temperature range of -10 to -55 °C. For 13 solvents at -39.6 °C, an extended Grunwald-Winstein equation correlation led to sensitivities to changes in solvent nucleophilicity of 0.56 and to changes in solvent ionizing power of 0.61. In 89.1% acetone at -20 °C, the comparison with acetyl bromide solvolysis led to a kOTs/kBr ratio of 1.4. In methanol and methanol-d at -39.6 °C, the solvent deuterium isotope effect k MeOH/kMeOD is 0.99. These results are consistent with an SNl reaction with appreciable nucleophilic solvation or an S N2 reaction with a loose transition state. These two approaches lead to similar structures for the transition state. A solution of the acetyl p-toluenesulfonate was conveniently prepared by the rapid reaction of acetyl chloride with silver p-toluenesulfonate in acetonitrile. Copyright 2013 John Wiley & Sons, Ltd. Correlation of the rates of solvolysis of acetic p-toluenesulfonic anhydride (acetyl p-toluenesulfonate) and a comparison with acetyl halides. Copyright

SYNTHESIS OF STERICALLY HINDERED SECONDARY AMINOETHER ALCOHOLS

Severely sterically hindered secondary aminoether alcohols are prepared by reacting organic carboxylic, organic carboxylic acid halides, acid anhydrides or a ketene with an alkyl, alkaryl or alkylhalo sulfonate to yield a sulfonic. Carboxylic anhydride compound which is then reacted with a dioxane to cleave the ring of the dioxane, yielding a cleavage product which cleavage product is then aminated with an alkylamine and hydrolyzed with base to yield the severely sterically hindered secondary aminoether alcohol.

Syntheses of 1-substituted furan-fused 3-sulfolenes and their Diels-Alder reactions

The preparation of 1-substituted 4H,6H-dihydrothienofuran 5,5-dioxides and their intermolecular Diels-Alder reactions with typical dienophiles are described. 1-Acetyl-1d and 1-nitro-furansulfolene 1e were prepared by simple new methods.Acetyl and nitro substituents in the furan moiety did little to diminish its Diels-Alder reactivity relative to the corresponding furans.Furthermore, on reaction with dimethyl fumarate, 1-acetylfuransulfolene 1d acted like the corresponding 3,4-dimethylenefuran.

SYNTHESES OF 2-SUBSTITUTED FURAN-ANNULATED 3-SULFOLENES AND THEIR DIELS-ALDER REACTIONS

The preparation of 2-substituted 4,6-dihydrothienofuran-5,5-dioxides (1b-e) and their intramolecular Diels-Alder reactions with typical dienophiles are described.

A novel and versatile route to mixed p-toluenesulphonic carboxylic anhydrides

A versatile route to the mixed p-toluenesulphonic carboxylic anhydrides (1) via the reaction of tetra-n-butylammonium carboxylate (2) with p-toluenesulphonyl chloride in a neutral medium is described.Some of the synthetic applications of the proposed method are described.