76377-04-3

Upstream product

• 2930-05-4 Benzyloxymethyl-oxiran 
• 15028-56-5 4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 100-51-6 benzyl alcohol 
• 100-44-7 benzyl chloride 
• 80525-59-3 4-[(benzyloxy)methyl]-3,6-dioxaoctane-1,8-dicarboxylic acid 
• 80525-60-6 4-Benzyloxymethyl-3,6-dioxa-1,8-octanediol 
• 19249-03-7 triethylene glycol di-(p-toluenesulfonate) 
• 114951-76-7 1-(benzyloxymethyl) triethylene glycol 
• 13071-59-5 3-benzyloxypropan-1,2-diol 
• 41024-91-3 penta(ethylene glycol) bis(p-toluenesulfonate) 
• 5197-65-9 1,14-dichloro-3,6,9,12-tetraoxatetradecane 

Downstream Products

• 70069-04-4 2-hydroxymethyl-18-crown-6 
• 83585-76-6 ((dodecyloxy)methyl)-18-crown-6 

Relevant academic research and scientific papers

Synthesis of Novel C-Pivot Lariat 18-Crown-6 Ethers and Their Efficient Purification

The syntheses of various lariat ethers including several not previously reported and their efficient purification are presented. The synthesis route brings together reactions from a variety of previous works leading to a robust and generalized approach to these C-pivot lariats. The main steps are condensation of functionalized diols with pentaethylene glycol ditosylate in the presence of potassium as a templating cation. Purification of the final products was achieved without chromatography by extracting from an aqueous potassium hydroxide solution.

Synthesis of lipophilic lariat ethers with pendant N-(X)sulfonyl carboxamide groups

Synthetic routes to sixteen lipophilic lariat ether N-(X)sulfonyl carboxamides with X = trifluoromethyl, methyl, phenyl, and p-nitrophenyl are described. For this new family of proton-ionizable lariat ethers in which the acidity can be 'tuned' by X group variation, the ring size is systematically varied from 12-crown-4 to 14-crown-4 to 15-crown-5 to 18-crown-6.

A CONVENIENT SYNTHESIS OF CROWN AND AZACROWN ETHERS WITH PENDANT OXIRANE GROUP

Synthesis of 4,5-epoxy-2-oxa-1-pentylcrown (I) and N-(2,3-epoxy-1-propyl)azacrown ethers (II) from accessible materials is described.

Neutral Ligands with Surfactant-Type Structure - Synthesis, Complexation, and Ion Transfer

New lipophilic neutral ligands which combine crown ether and podand characteristics with structural features of surfactants (cf. formulas 1-12, 16-26) were synthesized.Their complexation behaviour was studied, their solid-to-liquid and liquid-to-liquid phase transfer properties as well as their efficiency in ion transport across a liquid model membrane.Crystalline stoichiometric complexes of the cycles 2a-4a and of 3e with NaSCN, Ba(SCN)2, and BaI2 can be isolated.Among the noncyclic representatives a crystalline complex is obtained only from 11 with BaI2.The ligand 8d behaves in aqueous solution as a typical surfactant showing micelle formation and cloud point.

Synthesis and Alkali-cation Complexing Properties of 12-Crown-4 Derivatives

Benzyloxymethyl-12-crown-4, a precursor of hydroxymethyl-12-crown-4, is prepared in an excellent yield by the reaction of 3-benzyloxy-1,2-propanediol with 1,8-dichloro-3,6-dioxaoctane in the heterogeneous t-BuOLi/t-BuOH/LiBr*2H2O reaction system.The hydrogenolysis in the presence of p-toluenesulfonic acid leads to a good yield of hydroxymethyl-12-crown-4.The sandwich-type 2:1 complexation with Na+ of 12-crown-4 and hydroxymethyl-12-crown-4 derivatives was discussed on the basis of the stability constants and the solvent extraction in the CH2Cl2-water system.

ALTERNATIVE, SIMPLE ROUTE TO HYDROXYMETHYL CROWN ETHERS

Components for polymer-supported catalysts, hydroxymethyl-substituted 15-crown-5 and 18-crown-6 were prepared from readily available starting materials on relative simple way.