'Green' synthesis of nitro alcohols catalyzed by solid-supported tributylammonium chloride in aqueous medium.
A series of 1-aryl-2-nitroalkan-1-ols (5a-m; Table 2) was prepared in yields of 64-94% by Henry reaction between aromatic aldehydes and nitroalkanes in the presence of a dual catalytic system of KOH and polystyrene-supported tributylammonium chloride (PsTBAC; 2). The reactions were performed either in H2O containing 10% of THF or, in the case of liquid reagents (aldehydes and nitroalkanes), in neat H2O at room temperature. The immobilized phase-transfer catalyst, designed to be used for large-scale industrial processes, could be easily separated from the products, and effectively re-used several times, basically without loss in activity.
Wang
Zongting
Z
School of Chemistry & Chemical Engineering, Chinese University of Petroleum, Dongying, 257062, PR China. ztiwang@hdpu.edu.cn
Xue
Huiqing
H
Wang
Shuchao
S
Yuan
Cunguang
C
D002384:Catalysis; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D009574:Nitro Compounds; D000644:Quaternary Ammonium Compounds; C517377:tributylammonium chloride; D014867:Water