6500-50-1

Usage

InChI:InChI=1/C15H21NO4/c1-3-5-6-12(4-2)11-20-15(17)13-7-9-14(10-8-13)16(18)19/h7-10,12H,3-6,11H2,1-2H3

Upstream product

• 111-87-5 octanol 
• 99-77-4 ethyl 4-nitrobenzoate 
• 122-04-3 4-nitro-benzoyl chloride 
• 16156-52-8 n-octyl methanesulfonate 
• 3847-57-2 sodium 4-nitrobenzoate 
• 111-83-1 1-bromo-octane 
• 62-23-7 4-nitro-benzoic acid 
• 555-16-8 4-nitrobenzaldehdye 
• 619-73-8 4-nitrobenzyl chloride 

Downstream Products

• 14309-41-2 octyl ester of p-aminobenzoic acid 
• 1250441-36-1 4-(3-formyl-4-hydroxyphenylazo)benzoic acid octyl ester 
• 1250441-37-2 4-[4-hydroxy-3-(n-octyliminomethyl)phenylazo]benzoic acid octyl ester 

Relevant academic research and scientific papers

Sodium cyanide-promoted copper-catalysed aerobic oxidative synthesis of esters from aldehydes

A simple and efficient copper-catalysed procedure for oxidative esterification of aldehydes with alcohols and phenols mediated by sodium cyanide, using air as a clean oxidant, is described. A variety of aromatic aldehydes and structurally different alcohols and phenols reacted efficiently, and the product esters were obtained in good to excellent yields under normal atmospheric and solvent-free conditions.

Graphene Oxide: An Efficient Acid Catalyst for the Construction of Esters from Acids and Alcohols

Graphene oxide was found to be an efficient and reusable acid catalyst for the esterification reaction. A wide range of aliphatic and aromatic acids and alcohols were compatible with the standard conditions and afforded the corresponding products in good yields. The heterogeneous catalyst can be easily recovered and recycled in dichloro-ethane solvent with good catalytic activity.

A microwave-assisted highly practical chemoselective esterification and amidation of carboxylic acids

The ubiquitousness of esters and amide functionalities makes their coupling reaction one of the most sought-after organic transformations. Herein, we have described an efficient microwave-assisted synthesis of esters and amides. Soluble triphenylphosphine, in conjugation with molecular iodine, gave the desired products without the requirement for a base/catalyst. In addition, a solid-phase synthetic route is incorporated for the said conversion, which has added advantages over solution-phase pathways, such as low moisture sensitivity, easy handling, isolation of the product by simple filtration, and reusability. In short, our method is simple, mild, green, and highly chemoselective in nature.

Preparation of fluorous Yamaguchi reagents and evaluation of their reactivity in esterification

Fluorous Yamaguchi (FY) reagents bearing a perfluoroalkyl chain were prepared and employed in esterification reactions; the yields were similar to those obtained with the traditional Yamaguchi (TY) reagent. Fluorous benzoic acids derived from the FY reagents were separated easily after the reaction. GC analysis revealed that the initial rates of reaction with the FY reagents were higher than those with the TY reagent. The acidities of benzoic acids produced from the FY and TY reagents were predicted by DFT to be similar (1.20 and 0.96, respectively).

Base-free oxidation of alcohols to esters at room temperature and atmospheric conditions using nanoscale Co-based catalysts

The direct oxidation of alcohols to esters with molecular oxygen is an attractive and crucial process for the synthesis of fine chemicals. To date, the heterogeneous catalyst systems that have been identified are based on noble metals or have required the addition of base additives. Here, we show that Co nanoparticles embedded in nitrogen-doped graphite catalyze the aerobic oxidation of alcohols to esters at room temperature under base-free and atmospheric conditions. Our Co@C-N catalytic system features a broad substrate scope for aromatic and aliphatic alcohols as well as diols, giving their corresponding esters in good to excellent yields. This apparently environmentally benign process provides a new strategy with which to achieve selective oxidation of alcohols.

Selective Monoesterification of Symmetrical Diols Using Resin-Bound Triphenylphosphine

Coupling reactions to make esters and amides are among the most widely used organic transformations. We report efficient procedures for amide bond formation and for the monoesterification of symmetrical diols in excellent yields without any requirement for high dilution or slow addition using resin-bound triarylphosphonium iodide. Easy purification, low moisture sensitivity, and good to excellent yields of the products are the major advantages of this protocol.

Generally applicable and efficient esterification of aldehydes with alcohols catalyzed by cyclopalladated ferrocenylimine

The palladacycle-catalyzed esterification of a variety of aldehydes with alcohols was developed. This reaction allows formation of esters in moderate to excellent yields not only for various aldehydes but also alcohols. In addition, the esterification could proceed well under mild conditions with a low catalyst loading of 0.0625 mol%. Copyright

Esterification of free fatty acids (Biodiesel) using nano sulfated-titania as catalyst in solvent-free conditions

Nano sulfated titania was tested as catalyst for esterification of free fatty acids, specially methanolic and ethanolic esterification of stearic acid (biodiesels). Factorial design evidenced a positive effect of reaction temperature, amount of catalyst, and solvents on ester conversion. This nano-sized sulfated titania has been prepared by a sol-gel hydrothermal process. This prepared sulfated titania showed high catalytic activity in direct esterification of fatty acids as well as benzoic acids with various alcohols and phenols under solvent-free conditions. This method is of great value because of its environmentally benign character, easy handling, high yields, convenient operation, and green. FT-IR studies are shown that the catalyst can be reused for acylation without loss of catalytic activity.

Nickel(II) and palladium(II) complexes of azobenzene-containing ligands as dichroic dyes

A large series of complexes has been synthesized with two chelating, Schiff base azobenzene derivatives connected linearly by coordination to a central nickel(II) or palladium(II) ion. These compounds have the general formulas MII(OC6H3-2-CHNR-4-NdNC6H 4-4-CO2Et)2 [M = Ni; R = n-Bu (3c), n-C 6H13 (3d), n-C8H17 (3e), n-C 12H25 (3f), Ph (3g), OH (3h), C6H 4-4-CO2Et (3i). M = Pd; R = i-Pr (4a), t-Bu (4b), n-Bu (4c), n-C6H13 (4d), n-C8H17 (4e), n-C12H25 (4f), Ph (4g)], MII[OC 6H3-2-CHN(n-C8H17)-4-NdNC 6H4-4-CO2(n-C8H17)] 2 [M = Ni (9), Pd (10)], MII[OC6H 3-2-CHN(n-C8H17)-4-NdNC6H 4-4-C6H4-4-O(n-C7H 15)]2 [M = Ni (14), Pd (15)], and MII[OC 6H3-2-CHN(CMe2)-4-NdNC6H 4-4-CO2Et]2 [M = Ni (17), Pd (18); the CMe 2 groups are connected]. These compounds have been characterized by using various physical techniques including 1H NMR spectroscopy and matrix-assisted laser desorption/ionization (MALDI) mass spectrometry. Single-crystal X-ray structures have been obtained for two pro-ligands and five complexes (3e, 4e, 14, 15, and 17). The latter always show a strictly square planar arrangement about the metal center, except for the NiII complex of a salen-like ligand (17). In solution, broadened 1H NMR signals indicate distortions from square planar geometry for the bis-chelate NiII complexes. Electronic absorption spectroscopy and ZINDO -S (Zerner's intermediate neglect of differential overlap) and TD-DFT (time-dependent density functional theory) calculations show that the lowest energy transition has metal-to-ligand charge-transfer character. The λmax of this band lies in the range of 409-434 nm in dichloromethane, and replacing NiII with PdII causes small blue-shifts. Dichroic ratios measured in various liquid crystal hosts show complexation-induced increases with NiII, but using PdII has a detrimental effect.

Synthesis of long chain aromatic esters in a solvent-free procedure under microwaves

Alkylation with n-octyl bromide of several substituted benzoic acids was performed under solvent-free phase transfer catalysis with excellent yields (≥95%) within very short times (2-7 min). Terephthalate octylation was raised from 20% to 92% under microwave activation when compared to conventional heating thanks to intrinsic effects of the radiation.