88639-49-0

Upstream product

• 75-89-8 2,2,2-trifluoroethanol 
• 874-60-2 4-methyl-benzoyl chloride 
• 99-94-5 p-Toluic acid 
• 64-17-5 ethanol 
• 589-18-4 4-Methylbenzyl alcohol 
• 77253-67-9 trifluoroethanol-d₃ 

Downstream Products

• 75-89-8 2,2,2-trifluoroethanol 
• 937-21-3 4-methylperbenzoic acid 
• 99-94-5 p-Toluic acid 

Relevant academic research and scientific papers

Construction of Esters through Sulfuryl Fluoride (SO 2 F 2) Mediated Dehydrative Coupling of Carboxylic Acids with Alcohols at Room Temperature

A facile method for the construction of esters through dehydrative coupling of carboxylic acids with alcohols is developed. The reactions are mediated by sulfuryl fluoride (SO 2 F 2) at room temperature and proceed with high efficiency. The method has several advantages including broad substrate scope, mild conditions, excellent functional group compatibility and affords high yields, even on gram scale.

Concurrent pathways to explain solvent and substituent effects for solvolyses of benzoyl chlorides in ethanol-trifluoroethanol mixtures

Rate constants are reported at 25 °C for solvolyses of p-Z-substituted benzoyl chlorides (Z = O2N, Cl, H, Me, and MeO) in 2,2,2-trifluoroethanol (TFE) in binary mixtures with water or ethanol. Product selectivities (kTFE/kwater) are also reported. Previous work in which rate constants for solvolyses of benzoyl chlorides are correlated with σ constants is re-evaluated. V-shaped plots (assuming concurrent reactions) are constructed from logarithms of rate constants vs. σ (not σ ) for substituent effects or a suitable parameter for solvent effects. Conditions are established for which it is predicted that concurrent mechanisms (one dissociative, one associative) each contribute 50% towards the observed rate constants. ARKAT-USA, Inc.

METHOD FOR PRODUCING DEUTERATED PERFLUOROALYKYL METHANOL

PROBLEM TO BE SOLVED: To provide a method for safely and efficiently producing a deuterated perfluoroalykyl methanol. SOLUTION: This method for producing the deuterated perfluoroalykyl methanol expressed by general formula (I): RfCD2O-A (Rf is a perfluoroalkyl; and A is D or H) comprises reducing an perfluorcarboxylic acid anhydride expressed by general formula (II): (RfCO)2O by using deuterium in the presence of a transition metal catalyst.

Facile oxidative conversion of alcohols to esters using molecular iodine

A simple, efficient, and high-yield procedure for the oxidative conversion of alcohols to various types of esters and ketones, with molecular iodine and potassium carbonate was successfully carried out.

Facile conversion of alcohols to the corresponding 2,2,2-trifluoroethyl esters with molecular iodine and potassium carbonate in 2,2,2-trifluoroethanol

A simple, effective, and high-yield procedure for the oxidative conversion of primary alcohols to the corresponding 2,2,2-trifluoroethyl esters, with molecular iodine and potassium carbonate in 2,2,2-trifluoroethanol, was studied.

Mechanism of Solvolysis of Substituted Benzoyl Halides

Most substituted benzoyl fluorides undergo hydrolysis in aqueous solution through an associative mechanism with ρ = 1.7, kHOH/kDOD = 2.3+/-0.2, little dependence on the leaving group (kCl/kF = 1.2), and general-base catalysis by fluoride ion.There is an abrupt change to a dissociative mechanism through an acylium ion intermediate for the hydrolysis of p-(dimethylamino)benzoyl and (in part) p-anisoyl fluorides, with ρ+ =/Cl/kF = 10E6-10E7, and kHOH/kDOD = 1.1 for p-Me2NPhCOF.Common ion inhibition by fluoride ion traps the p-(dimethylamino)benzoyl acylium ion, which undergoes hydration with kh ca. 10E9-10E10 s-1.The increase in the solvent isotope effect for hydrolysis of p-(dimethylamino)benzoyl fluoride to kHOH/kDOD = 1.9 in the presence of concentrated potassium fluoride is attributed to general-base-catalyzed hydration of the acylium ion intermediate.The large yield of trifluoroethyl ester from the solvolysis of p-anisoyl fluoride in TFE/EtOH/HOH suggests that the acylium ion reacts in a solvent-separated ion pair, with kh ca. 10E12 s-1; extrapolation predicts rate constants of =/> 10E13 s-1 for the hydration of less stable acylium ions.A change in sensitivity to solvent ionizing power from m = 1.4 in water to m = 0 in 60percent ethanol for p-(dimethylamino)benzoyl fluoride suggests a change to an associative mechanism.Benzoyl fluorides and acylium ions show selectivity toward alcohols, with βnuc ca. 0.2.The absence of common ion inhibition for the solvolysis of several benzoyl chlorides in water or 90percent TFE/HOH is consistent with kh >10E11 s-1 for the acylium ions.Solvolysis occurs through the dissociative reaction channel, with ρ+ = -3.0, even when the estimated lifetimes of the acylium ion species suggest that there is no chemical barrier for their hydration.However, there is a change to an associative mechanism for the solvolysis of p-nitrobenzoyl chloride in water.