(S)-1-(2-Methoxyphenyl)ethanol

Base Information

• Chemical Name: (S)-1-(2-Methoxyphenyl)ethanol
• CAS No.: 108100-06-7
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.193
• European Community (EC) Number: 859-825-7
• Nikkaji Number: J231.903I
• Mol file: 108100-06-7.mol

Synonyms:(S)-1-(2-Methoxyphenyl)ethanol;108100-06-7;(1S)-1-(2-methoxyphenyl)ethanol;(1S)-1-(2-methoxyphenyl)ethan-1-ol;SCHEMBL3929903;(S)-1-(o-Methoxyphenyl)ethanol;(s)-1-(2-methoxy-phenyl)-ethanol;(S)-1-(2-methoxyphenyl)ethan-1-ol;AKOS016843339;Benzenemethanol, 2-methoxy-a-methyl-, (aS)-;EN300-82469;A806888;Z360055194

Chemical Property of (S)-1-(2-Methoxyphenyl)ethanol

Chemical Property:

• Boiling Point: 236℃
• PKA: 14.49±0.20(Predicted)
• Flash Point: 111℃
• PSA: 29.46000
• Density: 1.053
• LogP: 1.74850
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 152.083729621
• Heavy Atom Count: 11
• Complexity: 114

Purity/Quality:

98%min ^*data from raw suppliers

(1S)-1-(2-methoxyphenyl)ethan-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1OC)O
• Isomeric SMILES: C[C@@H](C1=CC=CC=C1OC)O

Technology Process of (S)-1-(2-Methoxyphenyl)ethanol

There total 81 articles about (S)-1-(2-Methoxyphenyl)ethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-Methoxyacetophenone (579-74-8) → (1S)-1-(2-methoxyphenyl)ethan-1-ol (13513-82-1,108100-06-7,111059-03-1,113724-48-4)

Guidance literature:

With lithium hydroxide; hydrogen; triphenylphosphine; iridium; (8R,9R)-9-amino(9-deoxy)epicinchonin; In methanol; at 40 ℃; for 20h; under 45004.5 Torr; optical yield given as %ee; enantioselective reaction;

DOI:10.1002/anie.200801809

Reference yield: 44.6%

1-(2-methoxyphenyl)ethanol (13513-82-1) → 2-Methoxyacetophenone (579-74-8) + (R)-1-(2-methoxyphenyl)ethanol (13513-82-1,108100-06-7,111059-03-1,113724-48-4)

Guidance literature:

With C₅₀H₄₂ClN₂O₃Ru; In chloroform; at 25 ℃; enantioselective reaction; Kinetics; Molecular sieve; Resolution of racemate;

DOI:10.1002/anie.201310426

Reference yield:

1-(2-methoxyphenyl)ethanol (13513-82-1) → 2-Methoxyacetophenone (579-74-8) + (1S)-1-(2-methoxyphenyl)ethan-1-ol (13513-82-1,108100-06-7,111059-03-1,113724-48-4) + (R)-1-(2-methoxyphenyl)ethanol (13513-82-1,108100-06-7,111059-03-1,113724-48-4)

Guidance literature:

With 3 A molecular sieve; oxygen; caesium carbonate; Pd(2,5-norbornadiene)Cl₂; (-)-sparteine; In chloroform; at 23 ℃; for 164h; under 760 Torr;

DOI:10.1002/anie.200352444

upstream raw materials:

sodium ethanolate

2-Methoxyacetophenone

o-methoxystyrene

dimethyl sulfate

Downstream raw materials:

(S)-1-benzoyloxy-1-(2-methoxy-phenyl)-ethane

(3,5-Dinitro-phenyl)-carbamic acid (R)-1-(2-methoxy-phenyl)-ethyl ester

(R)-1-(2-Naphthyl)ethanol

1-(2-methoxyphenyl)ethanol

Refernces

• 1、 Song, Chun,Ma, Changqin,Ma, Yudao,Feng, Wenhua,Ma, Shutao,Chai, Qiang,Andrus, Merritt B.. "Bis-paracyclophane N-heterocyclic carbene-ruthenium catalyzed asymmetric ketone hydrosilylation". . p. 3241 - 3244. Retrieved 2005.
• 2、 Jiang, He-Yan,Yang, Chao-Fen,Li, Chun,Fu, Hai-Yan,Chen, Hua,Li, Rui-Xiang,Li, Xian-Jun. "Heterogeneous enantioselective hydrogenation of aromatic ketones catalyzed by cinchona- and phosphine-modified iridium catalysts". . p. 9240 - 9244. Retrieved 2008.
• 3、 Yu, Shen Luan,Li, Yan Yun,Dong, Zhen Rong,Gao, Jing Xing. "Synthesis of novel chiral tetraaza ligands and their application in enantioselective transfer hydrogenation of ketones". . p. 395 - 398. Retrieved 2012.
• 4、 Cui, Yu Ming,Wang, Lai Lai,Kwong, Fuk Yee,Sun, Wei. "Asymmetric hydrogenation of aromatic ketones using new chiral-bridged diphosphine/diamine-Ru(II) complexes". . p. 1403 - 1406. Retrieved 2010.
• 5、 Liu, Shanshan,Li, Gao-Wei,Yang, Xiao-Chao,Zhang, De-Yang,Wang, Min-Can. "Dinuclear zinc complex catalyzed asymmetric methylation and alkynylation of aromatic aldehydes". . p. 7147 - 7156. Retrieved 2017.
• 6、 Ak, Buenyamin,Elma, Duygu,Meric, Nermin,Kayan, Cezmi,Isik, Ugur,Aydemir, Murat,Durap, Feyyaz,Baysal, Akin. "New chiral ruthenium(II)-phosphinite complexes containing a ferrocenyl group in enantioselective transfer hydrogenations of aromatic ketones". . p. 1257 - 1264. Retrieved 2013.
• 7、 Hayashi,Matsumoto,Ito. "Asymmetric hydroboration of styrenes catalyzed by cationic chiral phosphine-rhodium(I) complexes". . p. 601 - 612. Retrieved 1991.
• 8、 Li, Chun,Zhang, Lin,Liu, Hailong,Zheng, Xueli,Fu, Haiyan,Chen, Hua,Li, Ruixiang. "Heterogeneous asymmetric hydrogenation of aromatic ketones enhanced by silanols on highly monodispersed silica spheres". . p. 27 - 30. Retrieved 2014.
• 9、 Zhao, Mangzhu,King, Anthony O.,Larsen, Robert D.,Verhoeven, Thomas R.,Reider, Paul J.. "A convenient and economical method for the preparation of DIP-chloride(TM) and its application in the asymmetric reduction of aralkyl ketones". . p. 2641 - 2644. Retrieved 1997.
• 10、 Baratta, Walter,Ballico, Maurizio,Del Zotto, Alessandro,Siega, Katia,Magnolia, Santo,Rigo, Pierluigi. "Osmium pyme complexes for fast hydrogenation and asymmetric transfer hydrogenation of ketones". . p. 2557 - 2563. Retrieved 2008.