scholarly journals Biomass‐Derived Aromatics by Solid Acid‐Catalyzed Aldol Condensation of Alkyl Methyl Ketones

2020 ◽  
Vol 4 (10) ◽  
pp. 1900150
Author(s):  
Phillip Reif ◽  
Hannah Rosenthal ◽  
Marcus Rose
Nanomaterials ◽  
2021 ◽  
Vol 11 (3) ◽  
pp. 747
Author(s):  
Mahashanon Arumugam ◽  
Chee Keong Goh ◽  
Zulkarnain Zainal ◽  
Sugeng Triwahyono ◽  
Adam F. Lee ◽  
...  

Solid acid catalyzed cracking of waste oil-derived fatty acids is an attractive route to hydrocarbon fuels. HZSM-5 is an effective acid catalyst for fatty acid cracking; however, its microporous nature is susceptible to rapid deactivation by coking. We report the synthesis and application of hierarchical HZSM-5 (h-HZSM-5) in which silanization of pre-crystallized zeolite seeds is employed to introduce mesoporosity during the aggregation of growing crystallites. The resulting h-HZSM-5 comprises a disordered array of fused 10–20 nm crystallites and mesopores with a mean diameter of 13 nm, which maintain the high surface area and acidity of a conventional HZSM-5. Mesopores increase the yield of diesel range hydrocarbons obtained from oleic acid deoxygenation from ~20% to 65%, attributed to improved acid site accessibility within the hierarchical network.


2006 ◽  
Vol 8 (12) ◽  
pp. 1056 ◽  
Author(s):  
Mangesh G. Kulkarni ◽  
Rajesh Gopinath ◽  
Lekha Charan Meher ◽  
Ajay Kumar Dalai

Author(s):  
Douglass F. Taber

There has recently been a great deal of interest in the synthesis of natural products that promote neurite outgrowth. Emmanuel A. Theodorakis of the University of California, San Diego described (Angew. Chem. Int. Ed. 2011, 50, 3672) the preparation of one of the most potent (10 nM) of these, (–)-jiadifenolide 3. Fittingly, a key transformation en route to this highly oxygenated seco-prezizaane was the oxidative rearrangement of 1 to 2. The starting point for the synthesis was the commercially available diketone 4. Allylation followed by addition to 5 gave the prochiral triketone 6. Enantioselective aldol condensation following the Tu/Zhang protocol then delivered the bicyclic enone 7. Alkylation to give 8 proceeded with high diastereoselectivity, perhaps controlled by the steric bulk of the silyloxy group. Exposure of the protected ketone to the McMurry reagent PhNTf2 gave the enol triflate 9, which smoothly carbonylated to the lactone 10. Epoxidation with alkaline hydrogen peroxide followed by oxidation gave the carboxylic acid, which spontaneously opened the epoxide, leading to the bis lactone 1. With 1 in hand, the stage was set for the key oxidative rearrangement to 2. It was envisioned that epoxidation would generate the cis-fused 11, which on oxidation would undergo acid-catalyzed elimination to give 12. The newly freed OH would then be in position to engage the lactone carbonyl, leading to 2. In the event, oxidation of the epoxide with the Dess-Martin reagent required sonication for 2 h. The rearranged lactone, even though it was susceptible to further oxidation, was secured in 38% overall yield from 1. After hydrogenation and protection, preparation of the enol triflate 13 from the congested cyclopentanone necessitated the use of the more reactive Comins reagent. Hydrogenation of the trisubstituted alkene from coupling with Me3Al then required 90 atmospheres of H2 overpressure. Hydroxylation of the lactone 14 with the Davis oxaziridine followed by further oxidation to the ketone with the Jones reagent and deprotection then completed the synthesis of (–)-jiadifenolide 3.


2016 ◽  
Vol 58 (1) ◽  
pp. 36-112 ◽  
Author(s):  
Prasenjit Bhaumik ◽  
Paresh Laxmikant Dhepe
Keyword(s):  

2010 ◽  
Vol 101 (21) ◽  
pp. 8273-8279 ◽  
Author(s):  
Soo-Jin Kim ◽  
Adid Adep Dwiatmoko ◽  
Jae Wook Choi ◽  
Young-Woong Suh ◽  
Dong Jin Suh ◽  
...  
Keyword(s):  

1995 ◽  
Vol 35 (1-2) ◽  
pp. 13-22 ◽  
Author(s):  
Owen C. Feeley ◽  
Qun Sun ◽  
Richard G. Herman ◽  
Marie Johansson ◽  
Luca Lietti ◽  
...  

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