50623-57-9

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InChI:InChI=1/C13H26O2/c1-3-5-7-8-9-10-11-13(14)15-12-6-4-2/h3-12H2,1-2H3

Upstream product

• 112-05-0 nonanoic acid 
• 71-36-3 butan-1-ol 
• 688-74-4 boric acid tributyl ester 
• 111-83-1 1-bromo-octane 
• 201230-82-2 carbon monoxide 
• 592-84-7 n-butyl formate 
• 111-66-0 oct-1-ene 
• 91083-85-1 N-Butyl-N-nitrosopelargonamide 
• 74-89-5 methylamine 
• 109-65-9 1-bromo-butane 
• 141-32-2 acrylic acid n-butyl ester 
• 638-45-9 1-Iodohexane 
• 42474-15-7 N-Butylpelargonamide 
• 1041479-71-3 C₂₄H₅₁In 

Relevant academic research and scientific papers

Robust acidic pseudo-ionic liquid catalyst with self-separation ability for esterification and acetalization

The novel acidic pseudo-ionic liquid catalyst with self-separation ability has been synthesized through the quaternization of triphenylphosphine and the acidification with silicotungstic acid. The pseudo-IL showed high activities for the esterification with average conversions over 90%. The pseudo-IL showed even higher activities for acetalization than traditional sulfuric acid. The homogeneous catalytic process benefited the mass transfer efficiency. The pseudo-IL separated from the reaction mixture automatically after reactions, which was superior to other IL catalysts. The high catalytic activities, easy reusability and high stability were the key properties of the novel catalyst, which hold great potential for green chemical processes.

A simple route to 1,4-addition reactions by Co-catalyzed reductive coupling of organic tosylates and triflates with activated alkenes

An efficient Co-catalyzed 1,4-addition reaction of alkyl/aryl triflates and tosylates with activated alkenes is described. In this reaction, an air-stable cobalt(ii) complex, a mild reducing agent Zn and a simple proton source (H2O) are used. A radical mechanism for the addition of alkyl tosylates to activated alkenes is likely involved.

Synthesis of carboxylic acid esters in the presence of micro- and mesoporous aluminosilicates

The catalytic properties of zeolites HY, HBeta, and HZSM-12 and of mesoporous amorphous aluminosilicate in liquid-phase esterification of aliphatic (monobasic C1-C18, dibasic C6, C10) and aromatic (benzoic, trimellitic, phthalic) carboxylic acids with butanol were studied. Zeolite HBeta appeared to be the most active catalyst. Procedures were developed for preparing esters in the presence of zeolitic catalyst HBeta, ensuring 100% selectivity of ester formation at 90-98% conversion of the acid.

Palladium-catalyzed oxidative carbonylation of alkyl and aryl indium reagents with CO under mild conditions

CO now can react with organoindium reagents. A novel palladium-catalyzed oxidative carbonylation reaction of organoindium reagents by CO gas with desyl chloride as oxidant was developed in supplementation with the classical methods for preparation of carboxylic acid derivatives. Primary, secondary alkyl indium reagents with β-hydrogens and aryl indium reagents were suitable substrates, and the reaction could be carried out at 60°C under 50 psi CO. Carbonylation of alkyl indium reagents can occur smoothly without additional base. Although the indium reagents were prepared from corresponding Grignard reagents (at low temperature), they displayed full compatibility with various functional groups under the protic reaction conditions. Preliminary mechanistic studies including stoichiometric and catalytic reaction examination provided evidence to support the operation of the mechanism consisted of oxidative addition of deslyl chloride to Pd(0) and quick tautomerization to give a palladium enolate species II (ROPdCl), displacement of the enolate group in II by R2OH, followed by CO insertion to give alkoxycarbonyl palladium complex V, which undergoes transmetalation with R13ln and reductive elimination to afford the product and a Pd(0) species. In this mechanism, the alkoxycarbonyl group was transferred to the palladium center prior to the alkyl group, different from traditional ways initiated from oxidative addition of alkyl halides to a Pd(0) species.

Cobalt-catalyzed reductive coupling of saturated alkyl halides with activated alkenes

An efficient cobalt-catalyzed reductive coupling reaction of alkyl halides with electron-withdrawing alkenes (CH2=CR1EWG, EWG = electron-withdrawing group) in the presence of water and zinc powder in acetonitrile to give the corresponding Michael-type addition product (RCH 2CR1EWG) was described. The methodology is versatile such that unactivated primary, secondary, and tertiary alkyl bromides and iodides and various conjugated alkenes including acrylates, acrylonitrile, methyl vinyl ketone, and vinyl sulfone all successfully participate in this coupling reaction. For the alkyl halides used in the reaction, the iodides generally gave heller yields compared to those of the corresponding bromides. It is a unique method employing CoI2dppe, zinc, and alkyl halides, affording conjugate addition products in high yields. Mechanistically, the reaction appears to follow an oxidative addition driven route rather than the previously reported radical route.

Esterification of carboxylic acids catalyzed by in situ generated tetraalkylammonium fluorides

Esterification of carboxylic acids with alkyl halides can be efficiently catalyzed by tetrabutylammonium fluoride (TBAF) generated in situ from tetrabutylammonium hydrogensulfate (TBAHSO4) and KF·2H2O in THF. The general applicability and the characteristic feature of this approach has been amply demonstrated.

Regiochemical control in palladium(0) and palladium(II) catalysed alkene-formate ester carbonylation reactions

Palladium(0) complexes [Pd(PPh3)4 or Pd(dba) 2], (dba = dibenzylideneacetone) in the presence of 1,4-bis(diphenylphosphino)butane, can catalyse the reaction of alkenes and formate esters to give linear carboxylic esters as the major product, while the branched chain isomer was the principal ester obtained by use of a palladium(II) complex [bis(triphenylphosphine)palladium dichloride] as the catalyst.

Mono- and Bi-metallic Catalysed Formate-Halide Carbonylation Reactions

Benzylic, aryl, and alkyl halides react with formate esters and carbon monoxide, in the presence of the dimer of chloro(hexa-1,5-diene)rhodium(I), 2, to give carboxylic esters: bimetallic catalysis 2> is particularly beneficial when an aromatic halide is used as the substrate.

PALLADIUM(0) AND RHODIUM(I) CATALYSIS OF THE CARBONYLATION OF UNACTIVATED BROMIDES

Alkyl, vinyl, and aromatic bromides react with organoborates and carbon monoxide, in the presence of catalytic quantities of 1,5-hexadienerhodium(I) chloride dimer and tetrakis(triphenylphosphine)palladium(0), to give carboxylic esters in good yields.

NEW SYNTHETIC "TRICKS" USING OLD REAGENTS. A MILD METHOD FOR THE CONVERSION OF RCONHR' TO RCONHR''

N-Alkyl-N-nitrosoamides, RCON(NO)R'react with primary aliphatic amines (NH2R''), in refluxing dichloromethane or at room temperature, to give RCONHR'' in 65-98percent yields.