Asymmetric Hydrogenation of 3,5-Bistrifluoromethyl Acetophenone in Pilot Scale with Industrially Viable Ru/Diphosphine-Benzimidazole Complexes

Organic Process Research and Development

Volumn 18, Issue 9, 2014, Pages 1137-1141

  Xu, Liang ^a,b   Huang, Zhi Hong ^b   Sandoval, Christian A ^b   Gu, Lian Quan ^a   Huang, Zhi Shu ^a  

^a SUN YAT SEN UNIVERSITY   (China)

^b Zhongshan Torch Hi Tech Industrial Development Zone   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; KETONES;

ACETOPHENONES; AS-LIGANDS; ASYMMETRIC HYDROGENATION; ENANTIOMERIC EXCESS; PILOT SCALE; TRIFLUOROMETHYL;

HYDROGENATION;

EID: 84927511309     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op500148k     Document Type: Article

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18. Dinitration of p -xylene was prepared according to previously reported method,(16, 17) and the crude product could be used directly to synthesize 5c without purification. The conc. H2SO4 used was less than 500 mL in each batch, and it was easy to control safety. The synthesis of the 5c was prepared according to established methods. 5c was purified by using column chromatography. It was convenient and safe to obtain the 5c.
19. According to our experimental results, if 6a was adopted for the processing study, the AH product was required to do recrystallization at least twice to reach the required chiral purity (98%), because it is ee value was only 84%. Generally, the ee value of product should be decreased when the process was scaled up and it would lead to lower yield. After all things considered, 6c would be preferred to minimize the cost.
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