150-84-5Relevant articles and documents
Sn(II)-catalyzed β-citronellol esterification: A Bronsted acid-free process for synthesis of fragrances at room temperature
Da Silva,Julio,Dos Santos
, p. 1261 - 1266 (2015)
Simple SnCl2·2H2O was demonstrated to be able to catalyze β-citronellol esterification with acetic acid at room temperature under solvent-free conditions, achieving high conversion and ester selectivity (ca. 88% and 99%, respectively). Tin(ii) chloride is a stable and water-tolerant Lewis acid that is commercially available and less corrosive than Bronsted acid catalysts. This selective process is an attractive alternative to the mineral acid-catalyzed process because it avoids product neutralization common in those reactions. The effects of main reaction parameters such as reactant stoichiometry, temperature, solvent, and catalyst concentration were assessed. Among the tin catalysts evaluated, SnCl2 was the most active and selective. Moreover, SnCl2 was as active as sulfuric and p-toluenesulfonic acid catalysts, the Bronsted acids investigated herein, with additional advantages of being a solid and less corrosive catalyst.
Solid state acetylation with acetylimidazole: Selective protection of primary alcohols and phenols
Hagiwara, Hisahiro,Morohashi, Kimie,Suzuki, Toshio,Ando, Masayoshi,Yamamoto, Isao,Kato, Michiharu
, p. 2001 - 2006 (1998)
Primary alcohols and phenols have been acetylated with acetylimidazole by the solid state reaction, grinding both substrates with a pestle in a mortar.
Synthesis of citronellyl acetate via a transacetylation to citronellol from acetyl coenzyme A produced from glucose and acetate in growing yeasts
Oda, Shinobu,Sugai, Takeshi,Ohta, Hiromichi
, p. 500 - 501 (2001)
A novel coupling system, which is an acetylation system of primary alcohols with acetyl coenzyme A [acetyl-CoA] formed via the metabolism of glucose and acetate, was developed with Hansenula and Pichia. The supplementation of sodium acetate to glucose as the source of acetyl-CoA was effective to enhance the reaction rate and yield of acetylation of citronellol.
LUMINALLY-ACTING N-(PIPERIDIN-4-YL)BENZAMIDE DERIVATIVES
-
Paragraph 0219; 0220, (2021/11/13)
Disclosed are compounds of Formula 1, and pharmaceutically acceptable salts thereof, wherein m, R1, R2, R3, R4, R5, R6, X1, X2, X3 and X4 are defined in the specification. This disclosure also relates to materials and methods for preparing compounds of Formula 1, to pharmaceutical compositions which contain them, and to their use for treating diseases, disorders, and conditions associated with the 5-HT4 receptor.
Ring-Closing Metathesis of Aliphatic Ethers and Esterification of Terpene Alcohols Catalyzed by Functionalized Biochar
Kerton, Francesca M.,MacQuarrie, Stephanie L.,Vidal, Juliana L.,Wyper, Olivia M.
supporting information, p. 6052 - 6056 (2021/12/10)
Functionalized biochars, renewable carbon materials prepared from waste biomass, can catalyze transformations of a range of oxygen-containing substrates via hydrogen-bonding interactions. Good conversions (up to 75.2 %) to different O-heterocycles are obtained from ring-closing C?O/C?O metathesis reactions of different aliphatic ethers under optimized conditions using this heterogeneous, metal-free, and easy separable catalyst. The diversity in the sorts of O-containing feedstocks is further demonstrated by the utilization of functionalized biochar to promote the esterification of terpene alcohols, an important reaction in food and flavor industries. Under the optimized conditions, full conversions to various terpene esters are obtained. Moreover, both of the reactions studied herein are performed under neat conditions, thus increasing the overall sustainability of the process described.
Method for synthesizing acetate perfume
-
Paragraph 0063-0066, (2021/01/15)
The invention provides a method for synthesizing acetate by alcohol esterification, which comprises the following steps: by using enol acetate as an esterification reagent, esterifying a primary alcohol, secondary alcohol or tertiary alcohol substrate at high selectivity and high yield under the action of an acidic catalyst to obtain the corresponding acetate products. The method has the main advantages that the synthesis method is novel, enol acetate is used as an esterification reagent, reaction byproducts are micromolecular acetaldehyde or acetone and the like, and the micromolecular compounds do not show acidity and are low in boiling point, so that rearrangement side reaction of an alcohol substrate cannot be caused; and the small molecule byproduct can be conveniently removed from the reaction solution, so that the esterification reaction is promoted to be completely carried out, the reaction stability is good, and the yield is high.
IrIII-Catalyzed direct syntheses of amides and esters using nitriles as acid equivalents: A photochemical pathway
Talukdar, Ranadeep
supporting information, p. 5303 - 5308 (2020/04/17)
An unprecedented IrIII[df(CF3)ppy]2(dtbbpy)PF6-catalyzed simple photochemical process for direct addition of amines and alcohols to the relatively less reactive nitrile triple bond is described herein. Various amides and esters are synthesized as the reaction products, with nitriles being the acid equivalents. A mini-library of different types of amides and esters is made using this mild and efficient process, which uses only 1 mol% of photocatalyst under visible light irradiation (λ = 445 nm). The reaction strategy is also efficient for gram-scale synthesis.
Modified liquid–liquid interface cultivation system with floating microspheres and binder micro-pieces for slow-growing or unicellular microorganisms: Application to interfacial bioconversions with an actinomycete and yeasts
Oda, Shinobu,Nakanishi, Mami,Ishikawa, Asako,Baba, Toshiki
, p. 1 - 8 (2019/02/13)
Liquid–liquid interface bioreactor (L–L IBR) is a unique non-aqueous bioconversion system which comprises a hydrophobic organic solvent (upper phase), a fungal cells–floating microspheres (MS) layer (middle phase), and a liquid medium (lower phase). In this study, a modified L–L IBR with actinomycetes and yeasts was developed by using binder micro-pieces (BM) and estimated its availability through some bioconversions. This modified interface cultivation system was named a tacky liquid–liquid interface bioreactor (L–L IBRtac). After the detailed estimation of its characteristics, the system was applied to oxidation of citronellol to citronellal, 2-methylcyclohexanol to 2-methylcyclohexanone, and 2-octanol to 2-octanone with Rhodococcus hoagii NBRC 3730, oxidation of citronellal to citronellic acid with Candida viswanathii NBRC 10321, and transacetylation of citronellol by acetyl coenzyme A (acetyl-CoA) produced from glucose by Pichia kluyveri NBRC 1165. The accumulation of citronellal, 2-methylcyclohexanone, and 2-octanone reached 3.1 (16 days), 2.3 (12 days), and 32.9 g/l (12 days) in spite of strong biotoxicities of the substrates/products without collapse of a cells–MS–BM layer. On the other hand, 6.1 g/l of citronellic acid and 2.8 g/l of citronellyl acetate were produced from 5% citronellal and 10% citronellol for 12 days, respectively.
Continuous-Flow Chemo and Enzymatic Synthesis of Monoterpenic Esters with Integrated Purification
Adarme, Carlos A.A.,Le?o, Raquel A.C.,de Souza, Stefania P.,Itabaiana, Ivaldo,de Souza, Rodrigo O.M.A.,Rezende, Claudia M.
, p. 39 - 46 (2018/05/22)
Monoterpenic esters are very important flavor and fragrance compounds due to their organoleptic properties. Despite their importance, many drawbacks are found for the production of monoterpenic esters. Here in we report two different approach's (chemo and enzymatic) for the continuous production of monoterpenic esters with integrated purification arriving on the desired molecules with high yields (>95%) and short reaction times.
Formyloxyacetoxyphenylmethane and 1,1-diacylals as versatile O-formylating and O-acylating reagents for alcohols
Chapman, Robert S.L.,Francis, Molly,Lawrence, Ruth,Tibbetts, Joshua D.,Bull, Steven D.
, p. 6442 - 6452 (2018/10/02)
Formyloxyacetoxyphenylmethane, symmetric 1,1-diacylals and mixed 1-pivaloxy-1-acyloxy-1-phenylmethanes have been used as moisture stable O-formylating and O-acylating reagents for primary and secondary alcohols, allylic alcohols and phenols under solvent/catalyst free conditions to afford their corresponding esters in good yield.
