68367-32-8Relevant articles and documents
Diacyl Disulfide: A Reagent for Chemoselective Acylation of Phenols Enabled by 4-(N,N-Dimethylamino)pyridine Catalysis
Liu, Hong-Xin,Dang, Ya-Qian,Yuan, Yun-Fei,Xu, Zhi-Fang,Qiu, Sheng-Xiang,Tan, Hai-Bo
, p. 5584 - 5587 (2016)
A general and excellent acylation reagent, diacyl disulfide, was uncovered for efficient ester formation enabled by DMAP (4-(N,N-dimethylamino)pyridine) catalysis. This protocol offered a promising synthetic platform on site-selective acylation of phenolic and primary aliphatic hydroxyl groups, which greatly expanded the realm of protecting group chemistry. The importance of the reagent was also reflected by its excellent moisture tolerance, high efficiency, and potential in synthetic chemistry and biologically meaningful natural product modification.
Active and deactive modes of modified montmorillonite in p-cresol acylation
Venkatesha,Chandrashekara,Jai Prakash,Bhat
, p. 181 - 187 (2014/06/24)
para-Toluene sulphonic acid (p-TSA)-treated montmorillonite clay used as heterogeneous catalyst in acylation of para-cresol (PC) with aliphatic carboxylic acids. Reactions were studied under microwave and conventional modes of heating and reaction conditions were optimized by varying mole ratio, temperature, amount of catalyst and reaction time. Under optimized conditions the reaction was carried out involving p-cresol and decanoic acid. The reaction involved two steps, O-acylation involving ester formation followed by the Fries rearrangement involving C-acylation resulting in ketone product. Microwave heating mode showed higher conversion and the catalytic activity almost retained in repeated use. On the other hand the catalytic activity dropped by more than 50% in the case of conventional heating indicating rapid deactivation. A change in the color of the used catalyst was more intense in the case of conventional than in the microwave heating. Used catalysts were characterized for surface area and pore volume by BET technique, acidity by FTIR spectroscopy and amount of coke by TGA. Further investigations on the catalyst used in conventional heating revealed that the deactivation occurred during the O-acylation and not in the subsequent Fries rearrangement. However, the catalyst in the microwave irradiated reaction, exhibited a retarded rate of formation of coke precursors on the surface during O-acylation, thus preventing any decrease in catalytic activity. Present study indicates that the technique chosen for heating the reaction medium plays an important role in suppressing deactivation.
Direct esterification of carboxylic acids with p-cresol catalysed by acid activated Indian bentonite
Vijayakumar,Iyengar, Pushpa,Nagendrappa, Gopalpur,Prakash, B.S. Jai
, p. 1950 - 1953 (2007/10/03)
Acid activated Indian bentonite (AAIB) catalyst is used for the first time to esterify various carboxylic acids with p-cresol in average to excellent yields. Optimisation studies have been carried out for p-cresyl stearate synthesis. The catalyst is recoverable and recyclable.
