Functionalities such as acetamino groups or carbon–carbon double bonds in the thiol are not attacked under the mild reaction conditions and optically active thiol esters are obtained without racemization.33,78, Metal thiolates or benzenethiols in the presence of triethylamine also react very smoothly with diketene to yield S-alkyl (35)91 or S-aryl acetothioacetates (36).92 The β-keto thioesters (35) can be used in exceptionally mild preparations of β-keto amides (37),93 whereas (36) can be cyclized by Lewis acids to form thiocumarins (38).92 The S-t-butyl thiol ester (35) is also a suitable substrate for C-alkylation in the β-position or, after double deprotonation, in the δ-position (Scheme 3).91, Acylation of a simple thiol with an alkyl carboxylate is not a very suitable method for preparation of S-alkyl thiocarboxylates.
Vinyl acetate, an important industrial monomer, is prepared from acetic acid by the Zn(OAc)2/carbon catalyzed acetoxylation of acetylene, or by Pd/CuII catalyzed acetoxylation of ethylene (equations 105 and 106).257 Methyl, ethyl, n- and iso-butylacetates are important industrial solvents and methyl acetate could constitute a starting material in the catalytic synthesis of acetic anhydride.276 Cellulose acetate is extensively employed in the preparation of fibres and films.
1.0 Acetic acid is also a starting material for the synthesis of other industrial intermediates such as ketene (used in the synthesis of acetic anhydride, sorbic acid, etc.) 100 0.91 t-Butanol 95.9 The reaction between alcohol and acid anhydride is comparatively slower when compared to acid chloride. 14.4.1.
Ring opening by hydroxyl functionality ultimately results in both esterification and etherification, whereas base catalysis results predominantly in esterification.
26 1.1 Silica Chloride as a Mild and Efficient Reagent for Acetylation of Alcohols. A major drawback of their use is that they display poor atom efficiency, because half of their acylating equivalent is wasted as a carboxylate leaving group, which can be problematic when using valuable acyl donors (Figure 24(b)).13 The amide bond-forming reactions of acid anhydrides using primary amines as substrates may also form stable imides as unwanted side products.16 There are numerous reports of homogenous metal-catalyzed reactions using acid anhydride donors, with many metal complexes being used at very low catalyst loadings under mild conditions for the acetylation of electronically and sterically demanding amines.17 Notable reports of effective N-acylation catalysts that employ acid anhydrides as acyl donors include the use of indium triflate (Figure 24(c)),114 zinc oxide,115 heterogeneous yttria/zirconia (Figure 24(d)),116 and MoO2Cl2.117, Figure 24. 92.1 ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CHOUDHARY, VASANT RAMCHANDRA;MANTRI, KSHUDIRAM;JANA, SUMAN KUMAR;REEL/FRAME:011516/0702, Free format text:
26 0.2 It is, therefore, no surprise that there exist patents to convert phthalic anhydride to phthalic acid dichloride with carbonyl dichloride in the presence of catalysts.2,51–53 However, there are some methods available; thus α,α-di- chloromethyl methyl ether will convert acid anhydrides to acid chlorides31 and brenzcatechyl phosphorus tribromide will also achieve this transformation.36 Fluorides may be prepared similarly with the pyridine/HF mixture of Olah.50, Serban C. Moldoveanu, in Pyrolysis of Organic Molecules (Second Edition), 2019. The most preferred catalyst support, S, for said catalyst (IV) of this invention is Mont K-10 [Montmorillonite K-10]. benzoic acid ChemInform Abstract: An Extremely Powerful Acylation Reaction of Alcohols with Acid Anhydrides Catalyzed by Trimethylsilyl Trifluoromethanesulfonate..
Acetic anhydride α-Fluoro sulfides are conveniently prepared by the Pummerer-type reaction of sulfoxides with (diethylamino)sulfur trifluoride (DAST).110 Thallium(III) nitrate111 and phenyl iodosylbis(trifluoroacetate)112 have also been employed as activating agents in Pummerer-type reactions. Process for the esterification of normal alcohols by carboxylic acids using homogeneous acid catalyst, such as concentrated sulfuric acid, are well known in the prior art [Encyclopedia of Chemical Technology, Editor: Mary Howe-Grant, 4th Edition, John Wiley and Sons, vol. 0.03 Isobutylene and 2.9 Jackson, in Principles and Practice of Modern Chromatographic Methods, 2004.
Pyrolysis of this compound generates CO and various decomposition products involving, besides the anhydride functionality, the rest of the dehydroabietic acid . 1) Nucleophilic Attack by the Alcohol. gâ1)/Mont K-10 The reaction with phenol is …
26 Which member of each of the following pairs of compounds reacts faster with water? J.E. Simultaneously, residual aromatic carboxylic acid salt, which is derived from the MA, acts as a deprotonation agent, causing the esterification to progress and produce the desired carboxylic ester. The reaction was studied at pressures from about 0.7 to 20 Torr. Other products Examples of non-aqueous solvent are benzene, toluene, n-hexane, nitromtethane, ethylene dichloride, nitrobenzene, acetonitrile, etc. 1) By the process of this invention, a tertiary alcohol can be esterified by an acid anhydride to a corresponding ester with very high conversion (up to 100%) and high selectivity for the tertiary ester (above 95%), without producing appreciable amounts of tertiary alcohol dehydration products and/or any environmentally unacceptable product, using a reusable solid catalyst for a short reaction period, as short as 1.0 h. 2) Unlike the prior art process, the process of this invention is environment-friendly process; no toxic/corrosive product, like gaseous hydrogen halide is formed as a by product in the process of this invention.
In the Shiina esterification performed under basic conditions, asymmetric synthesis is realized using chiral nucleophilic catalysts.
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