2568-06-1Relevant academic research and scientific papers
A Direct Method for the Efficient Synthesis of Benzylidene Acetal at Room Temperature
Reddy, Narra Rajashekar,Kumar, Rashmi,Baskaran, Sundarababu
supporting information, p. 1548 - 1552 (2019/01/09)
For the first time, a metal-free direct method has been developed for the efficient synthesis of benzylidene acetal at room temperature using Dowex 50WX8 as a solid acid catalyst and Cl3CCN as a novel water scavenger. At room temperature, a wide variety of aryl and α,β-unsaturated aldehydes react readily with functionalized 1,2- and 1,3-diols to furnish the corresponding acetals in very good yields. Labile functional groups, like N-Boc, N-Cbz, -OTBDMS, -OBn, -N3 and acetonide are found to be stable under the reaction conditions. The versatility of this method is further demonstrated with carbohydrate substrates and optically active diols.
Reductive cleavage of acetals and ketals with 9-borabicyclo[3.3.1]nonane
Soderquist, John A.,Kock, Iveliz,Estrella, Maria E.
supporting information, p. 1076 - 1079 (2012/12/23)
The reductive cleavage of benzaldehyde acetals and acetophenone ketals with the air-stable crystalline 9-borabicyclo[3.3.1]-nonane dimer provides monobenzylated ether derivatives of diols and 1,2-oxygen-transposed β-phenethyl alcohols, respectively. The boron moiety is effectively recovered through simple procedures which involve convenient air-stable reagents and boron byproducts. The process is particularly selective for 1,3-diols giving the more substituted monobenzyl ether derivatives exclusively. With acetophenone ketals both reduction and elimination occur, permitting 9-BBN-H to hydroborate the resulting styrene to produce 1,2-oxygen-transposed β-phenethyl alcohols cleanly. Potential applications of this new process were illustrated with the synthesis of the hallucinogen, mescaline, and the analgesic, ibufenac.
