63537-05-3

Upstream product

• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 52755-39-2 (2E)-1-phenylbut-2-en-1-ol 
• 1896-62-4 (E)-benzalacetone 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 17488-65-2 4-phenylbut-3-en-2-ol 
• 14371-10-9 (E)-3-phenylpropenal 
• 82045-04-3 (rac)-(E)-2-acetoxy-4-phenylbut-3-ene 
• 32644-22-7 1-methyl-3-phenylallene 

Downstream Products

• 15325-63-0 (E)-3-methyl-1-phenyl-1-pentene 
• 78087-01-1 (S,E)-hex-4-en-3-ylbenzene 
• 78086-99-4 (R,Z)-hex-4-en-3-ylbenzene 
• 78087-00-0 (R,E)-hex-4-en-3-ylbenzene 
• 112528-98-0 (E)-(±)-2-methyl-4-phenylbut-3-enenitrile 
• 1219117-70-0 C₁₄H₂₁O₃PS 
• 107847-42-7 C₂₀H₂₂ 
• 107847-43-8 C₂₀H₂₂ 
• 92776-47-1 (+/-)-4-phenyl-oct-2Ξ-ene 
• 1104996-91-9 (E)-1-methyl-4-[1-methyl-3-phenyl-2-propen-1-yl]benzene 
• 1380425-95-5 (Z)-1-methyl-4-[1-methyl-3-phenyl-2-propen-1-yl]benzene 
• 1380425-96-6 (Z)-1-methoxy-4-[1-methyl-3-phenyl-2-propen-1-yl]benzene 
• 7302-00-3 (E)-1,3-diphenyl-1-butene 
• 7302-01-4 (Z)-(3-methyl-1-propene-1,3-diyl)dibenzene 

Relevant academic research and scientific papers

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

Chlorination of benzylic and allylic alcohols with trimethylsilyl chloride enhanced by natural sodium montmorillonite

A new and practical method for the efficient chlorination of tertiary, secondary, and primary benzylic and allylic alcohols is described. The method is characterized by the formation of hydrogen chloride from trimethylsilyl chloride and trace water, the formation of a carbenium ion through the protonation of an alcohol and subsequent dehydration, and the chlorination of the carbenium ion. During the process, sodium ion-exchanged montmorillonite plays a crucial role in capturing the generated hydrogen chloride, stabilizing the carbenium intermediate as well as promoting the chlorination.

Copper-catalyzed nucleophilic trifluoromethylation of allylic halides: A simple approach to allylic trifluoromethylation

Trifluoromethylation: The treatment of allylic halides with trifluoromethyltrimethylsilane in the presence of a catalytic amount of copper(I) thiophene-2-carboxylate (CuTC) gives the corresponding allylic trifluoromethylation products in good to high yields and with complete regioselectivity (see scheme). The use of THF as a solvent is crucial for obtaining good yields of product.

Development of a catalytic platform for nucleophilic substitution: Cyclopropenone-catalyzed chlorodehydration of alcohols

Cyclopropenone makes the switch: 2,3-Bis-(p-methoxyphenyl)cyclopropenone is a highly efficient catalyst for the chlorodehydration of 20 diverse alcohol substrates (see scheme; X=Cl). With oxalyl chloride as catalytic activator, this nucleophilic substitution proceeded through cyclopropenium-activated intermediates and resulted in complete stereochemical inversion in substrates with chiral centers.

Identification of a valuable kinetic process in copper-catalyzed asymmetric allylic alkylation

Copper bottomed: The application of a previously described process of dynamic kinetic asymmetric transformation to acyclic substrates allowed the identification of a relevant kinetic process in the title reaction (see scheme; CuTC= copper(I) thiophencarboxylate, Naphth= naphthyl). The optimization of the reaction conditions and generality of the method, as well as mechanistic considerations are disclosed.

One-pot formation of allylic chlorides from carbonyl derivatives

(Chemical Equation Presented) An efficient, one-pot method for the conversion of carbonyl electrophiles to allylic chlorides has been developed, by activating magnesium alkoxides in situ using TiCl4.

Tandem oxidation/halogenation of aryl allylic alcohols under Moffatt-Swern conditions

(Chemical Equation Presented) Aryl allylic alcohols are converted to halogenated unsaturated ketones or allylic halides using excess Moffatt-Swern reagent. Electron-poor aromatic rings favor formation of the halogenated ketone, while electron-donating substituents in the ortho or para positions favor formation of the allylic halide. The oxidation/halogenation reaction performs well with both oxalyl chloride and oxalyl bromide, providing access to the corresponding chlorides or bromides, respectively.

Cyanuric chloride-mediated synthesis of allylic chloride - Ipso- versus tele-substitution

Synthesis of unsymmetrical allylic chlorides has been accomplished using cyanuric chloride in combination with DMF through ipso-substitution and tele-substitution by judicious choice of the substituents at appropriate positions of unsymmetrical allyl alcohols, taking care of their electronic and steric properties. Copyright Taylor & Francis Group, LLC.

Acetyl chloride-ethanol brings about a remarkably efficient conversion of allyl acetates into allyl chlorides

AcCl-EtOH transforms primary and secondary allyl acetates into allyl chlorides that retain the olefinic bond in the more stable position. Whereas secondary allyl alcohols also react with almost the same efficacy as the acetates, the reactions of primary allyl alcohols that possess 1, 2-disubstituted alkenes are very slow. The products are isolated in high state of purity simply by removal of the volatiles.