155320-77-7

Basic information

• Product Name: Cyclohexanol, 2-methoxy-, (1R,2S)-
• CAS NO: 155320-77-7
• Molecular Formula: C7H14O2
• Molecular Weight: 130.187
• Mol File: 155320-77-7.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Cyclohexanol, 2-methoxy-, (1R,2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanol, 2-methoxy-, (1R,2S)-(155320-77-7)
• EPA Substance Registry System: Cyclohexanol, 2-methoxy-, (1R,2S)-(155320-77-7)

Safety Data

• Hazardous Substances Data: 155320-77-7(Hazardous Substances Data)

Upstream product

• 7429-44-9 2-methoxycyclohexanone 
• 90-05-1 2-methoxy-phenol 
• 155320-76-6 (2S)-2-methoxycyclohexanone 
• 90155-46-7 1R,2R-trans-diphenyl-1,2-ethanediamine 
• 109-76-2 Trimethylenediamine 

Relevant articles and documents

Ternary Alloys Enable Efficient Production of Methoxylated Chemicals via Selective Electrocatalytic Hydrogenation of Lignin Monomers

We explore the selective electrocatalytic hydrogenation of lignin monomers to methoxylated chemicals, of particular interest, when powered by renewable electricity. Prior studies, while advancing the field rapidly, have so far lacked the needed selectivity: when hydrogenating lignin-derived methoxylated monomers to methoxylated cyclohexanes, the desired methoxy group (-OCH3) has also been reduced. The ternary PtRhAu electrocatalysts developed herein selectively hydrogenate lignin monomers to methoxylated cyclohexanes - molecules with uses in pharmaceutics. Using X-ray absorption spectroscopy and in situ Raman spectroscopy, we find that Rh and Au modulate the electronic structure of Pt and that this modulating steers intermediate energetics on the electrocatalyst surface to facilitate the hydrogenation of lignin monomers and suppress C-OCH3 bond cleavage. As a result, PtRhAu electrocatalysts achieve a record 58% faradaic efficiency (FE) toward 2-methoxycyclohexanol from the lignin monomer guaiacol at 200 mA cm-2, representing a 1.9× advance in FE and a 4× increase in partial current density compared to the highest productivity prior reports. We demonstrate an integrated lignin biorefinery where wood-derived lignin monomers are selectively hydrogenated and funneled to methoxylated 2-methoxy-4-propylcyclohexanol using PtRhAu electrocatalysts. This work offers an opportunity for the sustainable electrocatalytic synthesis of methoxylated pharmaceuticals from renewable biomass.

Synthesis of ruthenium-hydride complexes and preparation procedures of chiral alcohols and ketones

trans-RuH(η1-BH4)[(S)-xylbinap][(S,S)-dpen] (0.00125 mmol), acetophenone (5.0 mmol), and 2-propanol (2.5 mL) were placed in an autoclave, and the resulting solution was repeatedly subject 5 times to a procedure of performing pressure reduction and argon introduction while stirring the solution for deaeration. A hydrogen tank was then connected to the autoclave, and after replacing the air inside an introduction tube with hydrogen, the pressure inside the autoclave was adjusted to 5 atmospheres and then hydrogen was released until the pressure dropped to 1 atmosphere. After repeating this procedure 10 times, the hydrogen pressure was adjusted to 8 atmospheres and stirring at 25° C. was performed for 12 hours. By concentrating the solution obtained by depressurization and subjecting the crude product to simple distillation, (R)-1-phenylethanol (yield: 95%) in the form of a colorless oily substance was obtained at an ee of 99%.

Hydrogenation of α-Keto Ethers: Dynamic Kinetic Resolution with a Heterogeneous Modified Catalyst and a Heterogeneous Base

The first successful example of the asymmetric hydrogenation of substituted α-keto ethers with Cinchona-modified Pt/Al2O3 is reported. In the absence of an additional base, kinetic resolution of the racemic starting material was observed with high diastereoselectivity and ee's up to 98% at conversions of a strong reaction acceleration but racemic product. Immobilization of OH- on solid ion exchangers resulted in the desired dynamic kinetic resolution, and ee's of >80% were obtained at >95% conversion. These effects are rationalized on the basis of a simple kinetic and structural model.