1058856-50-0

Basic information

• Product Name: C₁₂H₁₄Cl₂O₃
• Synonyms: C₁₂H₁₄Cl₂O₃
• CAS NO: 1058856-50-0
• Molecular Weight: 277.147
• Mol File: 1058856-50-0.mol

Chemical Properties

• CAS DataBase Reference: C₁₂H₁₄Cl₂O₃(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₂H₁₄Cl₂O₃(1058856-50-0)
• EPA Substance Registry System: C₁₂H₁₄Cl₂O₃(1058856-50-0)

Safety Data

• Hazardous Substances Data: 1058856-50-0(Hazardous Substances Data)

Upstream product

• 875018-47-6 ethyl (E)-4-(2,4-dichlorophenyl)-2-oxobut-3-enoate 
• 64-17-5 ethanol 
• 1327337-56-3 C₁₀H₁₀Cl₂O₃ 
• 108649-59-8 1-(2-bromoethyl)-2,4-dichlorobenzene 
• 1260521-21-8 C₁₀H₈Cl₂O₃ 

Relevant articles and documents

Highly enantioselective hydrogenation of 2-oxo-4-arybutanoic acids to 2-hydroxy-4-arylbutanoic acids

The Ru-catalyzed asymmetric hydrogenation of 2-oxo-4-arybutanoic acids to afford 2-hydroxy-4-arybutanoic acids was accomplished by employing SunPhos as chiral ligand and 1 M aq HBr as additive. The high enantioselectivities (88.4%-92.6% ee) and efficiency (TON=10,000, TOF=300 h-1) make this method efficient for the synthesis of an important intermediate, (R)-2-hydroxy-4-phenylbutanoic acid, for ACE inhibitors.

Direct asymmetric hydrogenation of 2-oxo-4-arylbut-3-enoic acids

A challenging direct asymmetric hydrogenation of (E)-2-oxo-4-arylbut-3- enoic acids to give 2-hydroxy-4-arylbutanoic acids (85.4-91.8% ee) was achieved with a Ru catalyst based on SunPhos as the chiral ligand. Further investigation of the reaction revealed that partial isomerization of 2-hydroxy-4-arylbutenoic acids was involved in the hydrogenation process. Employing the reaction conditions to the hydrogenation of 2-oxo-4-phenylbutanoic acid resulted in better enantioselectivity (91.8% ee) and efficiency (TON = 2000, TOF = 200 h-1), which offers a useful method for the synthesis of a common intermediate for ACE inhibitors.

Highly enantioselective sequential hydrogenation of ethyl 2-Oxo-4-arylbut-3-enoate to ethyl 2-hydroxy-4-arylbutyrate

(Chemical Equation Presented) The hydrogenation of (E)-ethyl 2-oxo-4-arylbut-3-enoate with [NH2Me2]+[{RuCl [(S)-SunPhos]}2(μ-Cl3)] gave ethyl 2-hydroxy-4- arylbutyrate with 94-96% ee. Further investigation has proved that the hydrogenation proceeded via a sequential hydrogenation of C=O and C=C bonds, which is sensitive to the reaction temperature. Hydrolysis of ethyl 2-hydroxy-4-phenylbutyrate (ee 93%) provided the 2-hydroxy-4-phenylbutyric acid with 81% yield at 99% ee after a single recrystallization from 1, 2-dichloroethylene.