Polymer‐Supported Sulfonic Acid

(strongly acidic catalyst) Alternate Names: Amberlyst 15, Amberlyst XN-1010, Dowex 50X8. Physical Data: cation-exchange resin cross-linked polystyrene divinylbenzene copolymer. Solubility: insoluble in all common solvents. Form Supplied in: widely available light brown solid; Amberlyst® and Amberlyte® are registered trademarks of Rohm & Haas Co; Dowex® is a registered trademark of Dow Chemical Co. Loading capacity: determined by titration; Amberlyst 15: 4.6 meq g−1; 1.8 meq mL−1; Dowex 50X8: 4.8 meq g−1; 1.8 meq mL−1. Purification: Amberlyst 15 is soaked in methanol for 24 h, washed with methanol, than THF and dried in vacuum.1 Commercially available material often gives best results if washed and dried prior to use. Handling, Storage, and Precautions: best if stored in closed bottles at room temperature. Amberlyst 15 is affected strongly by electrostatic charge and is highly hydroscopic.2 Dry resins expand when wetted. Can form explosive mixtures with acids and strong oxidizing agents; avoid contact with skin and eyes.3

[1]  L. T. Scott,et al.  2,5-Dimethylfuran. An Application of Ion Exchange-Resin Catalysis in Organic Synthesis , 2002 .

[2]  Kabza,et al.  Microwave-induced esterification using heterogeneous acid catalyst in a low dielectric constant medium , 2000, The Journal of organic chemistry.

[3]  Guigen Li,et al.  Highly Efficient Deprotection of N-p-Toluenesulfinyl Group of β-Branched Baylis–Hillman Adducts by Using Amberlite IR-120 (Plus) Ion-Exchange Resin , 2000 .

[4]  Y. Queneau,et al.  Selective Synthesis of 4,6-O-Alkenylidene and -Benzylidene Acetals from Unprotected Sucrose by Lanthanide(III) Resin-Catalyzed Transacetalization , 2000 .

[5]  Steven V. Ley,et al.  Multi-step organic synthesis using solid-supported reagents and scavengers: a new paradigm in chemical library generation , 2000 .

[6]  J. Fischer,et al.  Baeyer–Villiger-oxidation of cyclopentanone with aqueous hydrogen peroxide by acid heterogeneous catalysis , 1999 .

[7]  J. S. Sandhu,et al.  AMBERLYST-15(H+)-NABH4-LICL : AN EFFECTIVE REDUCTOR FOR OXIMES AND HYDRAZONES , 1999 .

[8]  J. Bussolari,et al.  Parallel synthesis of 2-alkoxy and 2-acyloxyphenylpropyl amides and amines using dihydrocoumarins as versatile synthons. Application of a novel resin quench-capture method , 1999 .

[9]  S. Ley,et al.  Three-step synthesis of an array of substituted benzofurans using polymer-supported reagents , 1999 .

[10]  S. Ley,et al.  Clean synthesis of α-bromo ketones and their utilisation in the synthesis of 2-alkoxy-2,3-dihydro-2-aryl-1,4-benzodioxanes, 2-amino-4-aryl-1,3-thiazoles and piperidino-2-amino-1,3-thiazoles using polymer-supported reagents , 1999 .

[11]  Masahiko Saitoh,et al.  Selective Monotetrahydropyranylation of Symmetrical Diols Catalyzed by Ion-Exchange Resins , 1998 .

[12]  D. Bergbreiter,et al.  Simultaneous Deprotection and Purification of BOC-amines Based on Ionic Resin Capture , 1998 .

[13]  S. Buchwald,et al.  CONVENIENT TWO-STEP CONVERSION OF LACTONES INTO CYCLIC ETHERS , 1998 .

[14]  S. Ley,et al.  Clean six-step synthesis of a piperidino-thiomorpholine library using polymer-supported reagents , 1998 .

[15]  M. Siegel,et al.  The Application of High-Throughput Synthesis And Purification To The Preparation Of Ethanolamines , 1997 .

[16]  R. Devraj,et al.  Chemical Library Purification Strategies Based on Principles of Complementary Molecular Reactivity and Molecular Recognition , 1997 .

[17]  P. Armas,et al.  Sodium borohydride-amberlyst-15 (H+): An effective reductor for hindered and unreactive ketones in aprotic solvent , 1997 .

[18]  S. Bott,et al.  Lanthanide-Promoted Reactions of Aldehydes and Amine Hydrochlorides in Aqueous Solution. Synthesis of 2,3-Dihydropyridinium and Pyridinium Derivatives. , 1997, The Journal of organic chemistry.

[19]  M. Kočevar,et al.  A NEW CONVENIENT BROMINATION WITH KBRO3/KBR/DOWEX , 1996 .

[20]  G. Righi,et al.  Regioselective opening of 3-Substituted N-Ethoxycarbonyl aziridine-2-carboxylates with metal halides toward the preparation of α and β-amino acids , 1996 .

[21]  Karl T. Chuang,et al.  Kinetics of acetic acid esterification over ion exchange catalysts , 1996 .

[22]  D. Schinzer,et al.  Amberlyst 15: A Versatile Catalyst for Silicon-Terminated Cyclizations , 1994 .

[23]  Manish Sharma,et al.  Esterification of carboxylic acids with olefins using cation exchange resins as catalysts , 1990 .

[24]  G. Majetich,et al.  Intramolecular reactions of unactivated alkenes with conjugated dienones , 1990 .

[25]  R. Ballini,et al.  A New Procedure for Dethioacetalization via Equilibrium Exchange with Aqueous Acetone,Paraformaldehyde and Amberlyst-15 as Acidic Catalyst." , 1990 .

[26]  R. Ballini,et al.  Amberlyst 15: A Practical, Mild and Selective Catalyst for Methyl Esterification of Carboxylic Acids.1 , 1988 .

[27]  R. Ballini,et al.  Amberlyst 15, a superior, mild, and selective catalyst for carbonyl regeneration from nitrogeneous derivatives , 1988 .

[28]  A. Alexakis,et al.  Mild protection and deprotection of alcohols as ter-butyl ethers in the field of pheromone synthesis , 1988 .

[29]  G. Coppola.  Amberlyst-15, A Superior Acid Catalyst for the Cleavage of Acetals , 1984 .

[30]  W. Greenlee,et al.  Mild conversion of carboxamides and carboxylic acid hydrazides to acids and esters , 1981 .

[31]  A. Bongini,et al.  A Simple and Practical Method for Tetrahydropyranylation of Alcohols and Phenols , 1979 .

[32]  R. Beier,et al.  A Facile Removal of the Tetrahydropyranyl Protecting Group from Alcohol Derivatives , 1979 .

[33]  M. Nagler,et al.  A rapid and convenient technique for converting ketones into their ethylenedioxy- or trimethylenedioxy-derivatives, and for making acetonides , 1979 .

[34]  Shyam K. Gupta.  New reactions and reagents. 5. Ketalization of 1,3-dihydroxy-2-propanone with alkanols. Formation of acyclic and cyclic ethers derived from pyruvic aldehyde , 1976 .

[35]  S. Dev,et al.  Amberlyst-15, a Superior Catalyst for the Preparation of Enol Ethers and Acetals , 1974 .