5457-78-3

Usage

InChI:InChI=1/C14H20O2/c1-2-3-4-5-9-12-14(15)16-13-10-7-6-8-11-13/h6-8,10-11H,2-5,9,12H2,1H3

Upstream product

• 111-64-8 n-octanoic acid chloride 
• 108-95-2 phenol 
• 124-07-2 Octanoic acid 
• 100-66-3 methoxybenzene 
• 111-87-5 octanol 
• 124-13-0 Octanal 
• 106-32-1 octanoic acid ethyl ester 

Downstream Products

• 102946-00-9 1-(4-octanoyloxy-phenyl)-octan-1-one 
• 124-07-2 Octanoic acid 
• 2589-73-3 1-(4-hydroxyphenyl)octanone 
• 108-95-2 phenol 
• 1089700-47-9 C₁₄H₂₂N₂O 
• 13222-43-0 bis(2-hydroxy-5-n-octylphenyl)methane 
• 70659-87-9 N-benzyloctanoic amide 
• 73318-92-0 2-hydroxy-5-octylbenzaldehyde 
• 1806-26-4 p-Octylphenol 

Relevant academic research and scientific papers

Visible-Light-Driven Dehydrogenative Coupling of Primary Alcohols with Phenols Forming Aryl Carboxylates

A preparative method for obtaining aryl esters from aliphatic primary alcohols and phenols was developed. The reaction proceeds under the irradiation of visible light at ambient temperature, dispensing with any oxidant or hydrogen acceptor. Primary alcohols having a variety of functional groups are successfully esterified with phenols. The produced esters can be utilized as the precursor of various carbonyl compounds.

One for Many: A Universal Reagent for Acylation Processes

This work describes acylation reactions facilitated by a type of heterocycle-based acyl transfer agent, 2-acyloxypyridazinone. Reactions of 2-acyloxypyridazinone with carboxylic acids yield mixed carbonic anhydride intermediates, which are reactive and could be coupled with a wide range of substrates including acids, amines, alcohols, and thiols. The wide substrate scope, ease of operation (no additive or catalyst), storage and handling stability, and atom-efficiency from recycling the heterocycle carrier make the reported acylating agent attractive for acylation-based coupling reactions.

Friedel-Crafts acylation of anisole with octanoic acid over acid modified zeolites

Friedel-Crafts acylation of anisole using octanoic acid as a green acylating agent was studied over zeolites free of solvent. It was found that a mixed organic acid, composed of tartaric acid and oxalic acid, modified Hβ (Mix-Hβ) zeolite showed the best catalytic performance among the catalysts studied. The conversion of octanoic acid and the selectivity for p-octanoyl anisole were 72.7% and 82.5%, respectively. Inductively coupled plasma analysis (ICP) and 27Al MAS NMR indicated dealumination of the parent Hβ zeolite due to the treatment of the mixed organic acid, leading to more accessible active sites and accounting for the better catalytic activity of the Mix-Hβ zeolite. Furthermore, lower strength of Lewis acid sites and Broensted acid sites of the Mix-Hβ zeolite, as demonstrated by Fourier Transform Infrared Spectrometry after adsorption of pyridine (Py-IR), are advantageous to suppress the demethylation of anisole and the subsequent esterification of thus formed phenol, accounting for its higher selectivity toward p-octanoyl anisole.

N-heterocyclic carbene-catalyzed oxidation of aldehydes for the synthesis of amides via phenolic esters

N-heterocyclic carbene-catalyzed oxidation using TEMPO is reported for the conversion of aldehydes to amides. A wide range of amides were synthesized in good yields (up to 72%) via a one-pot, sequential protocol involving oxidative esterification of aldehydes and subsequent aminolysis. To promote efficient aminolysis, various alkoxide leaving groups were evaluated.

Synthesis and critical micelle concentration of a series of gemini alkylphenol polyoxyethylene nonionic surfactants

A series of gemini n-alkylphenol polyoxyethylene surfactants (GAP) were successfully synthesized and their molecular structure were confirmed by NMR and FTIR spectrum. Using the same synthesis route, a Gemini nonylphenol polyoxyethylene surfactant (GNP) was synthesized using an industrial nonylphenol product and paraformaldehyde, and its molecular structure was also characterized by 1H-NMR and FTIR spectra. The optimal reaction conditions were established. The critical micelle concentration (CMC) values of GAP were determined by means of Wilhelmy plate method and steady-state fluorescence probe method. The experimental results show how the lengths of the hydrophilic polyoxyethylene chain and the hydrophobic tail alter the CMC values. The CMC values of the GAP are found to be much lower than those of corresponding conventional single tail nonionic surfactants of the polyethoxylated alkylphenol type, which indicates that the gemini species exhibit a better surface activity. AOCS 2011.

Effective esterification of carboxylic acids using (6-oxo-6H-pyridazin-1-yl)phosphoric acid diethyl ester as novel coupling agents

(6-Oxo-6H-pyridazin-1-yl)phosphoric acid diethyl esters (3) are efficient and selective coupling agents for equimolar esterification of carboxylic acids and alcohols. Esterification of aliphatic and aromatic carboxylic acids with aliphatic and aromatic alcohols using 3 afforded the corresponding esters chemoselectively in good to excellent yield.

ZrOCl2·8H2O: An efficient, cheap and reusable catalyst for the esterification of acrylic acid and other carboxylic acids with equimolar amounts of alcohols

Esterifications of carboxylic acids with equimolar amount of alcohols could be efficiently catalyzed by ZrOCl2·8H2O. Acrylate esters were obtained in good yields under solvent-free conditions at ambient temperature. The esterification of other carboxylic acids with alcohols also proceeded at ambient temperature or at 50°C to afford esters in high yields. If the esterification was performed in toluene under azeotropic reflux conditions to remove water, both the catalytic activity of ZrOCl 2·8H2O and the rate of esterification could be increased greatly. Furthermore, in the present catalytic system, the esters could be easily separated from the reaction mixtures and the catalyst could be easily recovered and reused.

An eco-friendly method for the synthesis of aryl and alkyl esters of carboxylic acids using acid activated Indian bentonite

Esterification of various carboxylic acids with phenol and alcohols has been achieved using acid activated Indian bentonite (AAIB) as catalyst. The catalyst is versatile, and the reaction is found to work well for primary, secondary and tertiary alcohols. The yields are very good under specific reaction conditions.

METHOD FOR PRODUCING AROMATIC ESTER

PROBLEM TO BE SOLVED: To provide a method for producing a high-purity aromatic ester in a high yield without using an aqueous medium as a reaction solvent. SOLUTION: This method for producing the aromatic ester comprises reacting an organic carboxylic acid halide with a phenol in the presence of a Lewis acid in an organic solvent. The concrete example of a preferable Lewis acid is a zinc compound such as zinc chloride, zinc bromide, zinc acetate, an aluminum compound such as aluminum chloride, aluminum bromide, diethylaluminum chloride, a boron compound such as boron trifluoride, boron trichloride, a titanium compound such as titanium tetrachloride, a zirconium compound such as zirconium chloride, and a tin compound such as tin tetrachloride, tin trichloride. A (meth)acrylic acid halide is preferable as the organic carboxylic acid halide.

Mapping the substrate selectivity and enantioselectivity of esterases from thermophiles

To identify potential applications of nineteen esterases from thermophiles, we mapped their substrate selectivity and enantioselectivity using a library of 50 esters. We measured the selectivities colorimetrically using Quick E, which uses pH indicators to detect hydrolysis and a chromogenic reference compound as an internal control. The substrate selectivity mapping revealed one esterase, E018b, with a strong preference for acetyl esters (14- to 25-fold over hexanoate). The enantioselectivity mapping revealed a number of cases of high enantioselectivity. Thirteen of the 19 esterases showed moderate or better enantioselectivity (>19) toward 1-phenethyl butyrate favoring the (R)-enantiomer and two esterases (E008, E013) showed moderate or better enantioselectivity (>20) toward methyl 2-chloropropionate favoring the (S)-enantiomer. Three esterases (E001, E004, E005) showed high (>46) enantioselectivity toward menthyl acetate favoring the (R)-enantiomer. This rapid mapping of the selectivity simplifies the characterization of new enzymes.