660-65-1

Upstream product

• 2536-36-9 16-iodohexadecanoic acid 
• 506-13-8 16-hydroxyhexadecanoic acid 
• 36575-67-4 16-hydroxyhexadecanoic acid methyl ester 

Relevant academic research and scientific papers

A new method for the lactonization of ω-hydroxy carboxylic acids with Di-2-thienyl carbonate by the promotion of DMAP and iodine

Successive reactions of ω-hydroxycarboxylic acids with an equimolar amount of di-2-thienyl carbonate (2-DTC) in the presence of a catalytic amount of 4-(dimethylamino)pyridine (DMAP) followed by an addition of 2-4 equimolar amounts of iodine afforded the corresponding lactones in good to high yields. Copyright

A new method for the synthesis of carboxylic esters and lactones with di-2-thienyl carbonate (2-DTC) by the promotion of DMAP and iodine

The esterification of carboxylic acids with alcohols by using di-2-thienyl carbonate (2-DTC) in the presence of a catalytic amount of 4-(dimethylamino) pyridine (DMAP) proceeded smoothly to afford the corresponding esters in good-to-high yields along with 2(5H)-thiophenone. This esterification was accelerated by the addition of an equimolar amount of iodine to afford the esters in higher yields within a shorter reaction time. Further, cyclization of ω-hydroxycarboxylic acids with an equimolar amount of 2-DTC in the presence of a catalytic amount of DMAP, followed by the addition of 1-4 equimolar amounts of iodine, afforded the corresponding lactones in good-to-high yields under mild conditions. This method was successfully employed in the synthesis of erythro-aleuritic acid lactone.

Efficient method for the lactonization of ω-hydroxycarboxylic acids with di-2-thienyl carbonate by the promotion of catalytic amounts of DMAP and Hf(OTf)4

An efficient method for the synthesis of macrolides from ω-hydroxycarboxylic acids is established by using an equimolar amount of di-2-thienyl carbonate (2-DTC) and catalytic amounts of 4-(dimethylamino) pyridine (DMAP) and group 4 metal triflates such as hafnium(IV) trifluoromethanesulfonate (Hf(OTf)4). Copyright

An effective method for the synthesis of carboxylic esters and lactones using substituted benzoic anhydrides with Lewis acid catalysts

An efficient mixed-anhydride method for the synthesis of carboxylic esters and lactones using benzoic anhydride having electron withdrawing substituent(s) is developed by the promotion of Lewis acid catalysts. In the presence of a catalytic amount of TiCl2(ClO4)2, various carboxylic esters are prepared in high yields through the formation of the corresponding mixed-anhydrides from 3,5-bis(trifluoromethyl)benzoic anhydride and carboxylic acids. The combined catalyst consisting of TiCl 2(ClO4)2 together with chlorotrimethylsilane functions as an effective catalyst for the synthesis of carboxylic esters from free carboxylic acids and alcohols with 4-(trifluoromethyl)benzoic anhydride. Various macrolactones are prepared from the free ω-hydroxycarboxylic acids by the combined use of 4-(trifluoromethyl)benzoic anhydride and titanium(IV) catalysts together with chlorotrimethylsilane under mild reaction conditions. The lactonization of trimethylsilyl ω-(trimethylsiloxy) carboxylates using 4-(trifluoromethyl)benzoic anhydride is also promoted at room temperature in the presence of a catalytic amount of TiCl 2(ClO4)2. An 8-membered ring lactone, a synthetic intermediate of cephalosporolide D, is successfully synthesized according to this mixed-anhydride method using 4-(trifluoromethyl)benzoic anhydride by the promotion of a catalytic amount of Hf(OTf)4.

A new method for the polymer-supported synthesis of cyclic oligoesters for potential applications in macrocyclic lactone synthesis and combinatorial chemistry

Attachment of ω-hydroxyalkanecarboxylic acids to Merrifield beads followed by treatment with a catalytic amount of di-n-butyltin oxide in chlorobenzene at 133 °C for 4-18 h brought about the formation of the corresponding cyclic oligomers (COs) as the mai

Scandium trifluoromethanesulfonate as an extremely active Lewis acid catalyst in acylation of alcohols with acid anhydrides and mixed anhydrides

Scandium trifluoromethanesulfonate (triflate), which is commercially available, is a practical and useful Lewis acid catalyst for acylation of alcohols with acid anhydrides or the esterification of alcohols by carboxylic acids in the presence of p-nitrobenzoic anhydrides. The remarkably high catalytic activity of scandium triflate can be used for assisting the acylation by acid anhydrides of not only primary alcohols but also sterically-hindered secondary or tertiary alcohols. The method presented is especially effective for selective macrolactonization of ω-hydroxy carboxylic acids.

A Novel Method for the Preparation of Macrolides from ω-Hydroxycarboxylic Acids

An efficient method for the synthesis of macrolides directly from ω-hydroxycarboxylic acids is established by using 4-(trifluoromethyl)benzoic anhydride and a catalytic amount of active titanium(IV) salts together with chlorotrimethylsilane under mild conditions.

Tin(IV)-catalyzed lactonization of ω-hydroxy trifluoroethyl esters

1,1,1-Trifluoroethyl esters of ω-hydroxycarboxylic acids were prepared and their conversion to macrocyclic lactones, including ricinelaidic lactone, was studied in the presence of catalytic quantities of tin(IV) reagents; a mechanism involving exchange of alkoxytrialkyltin species is proposed.

MACROCYCLIC LACTONES VIA BIOCATALYSIS IN NON-AQUEOUS MEDIA

The enantiospecificity of lipase-catalyzed lactonization of chiral (w-1)-hydroxy acids to form diolides in non-aqueous medium was investigated.

LIPASE CATALYZED SYNTHESIS OF MACROCYCLIC LACTONES IN ORGANIC SOLVENTS

A new method for the preparation of macrocyclic lactones from ω-hydroxyacid methyl esters is described.The approach utilizes intramolecular transesterification catalyzed by lipase in organic solvents.The procedure is also applicable to the synthesis of asymmetric lactones.