(+/-)-alpha-methylhydrocinnamic acid

Base Information

• Chemical Name: (+/-)-alpha-methylhydrocinnamic acid
• CAS No.: 5628-72-8
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.204
• Mol file: 5628-72-8.mol

Synonyms:ALPHA-METHYLHYDROCINNAMIC ACID

Chemical Property of (+/-)-alpha-methylhydrocinnamic acid

Chemical Property:

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-alpha-methylhydrocinnamic acid

There total 93 articles about (+/-)-alpha-methylhydrocinnamic acid 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-Benzyl-2-propenoic acid (5669-19-2) → 2-methyl-3-phenylpropionic acid (1009-67-2,5628-72-8,14367-54-5,14367-67-0)

Guidance literature:

With C₄₈H₅₀Cl₄N₂O₂P₂Ru₃; hydrogen; sodium hydrogencarbonate; In methanol; at 20 ℃; for 24h; under 3750.38 Torr; enantioselective reaction; Autoclave;

DOI:10.1021/acs.orglett.6b00748

Reference yield: 97.0%

2-methyl-3-phenylacrylic acid (1895-97-2) → 2-methyl-3-phenylpropionic acid (1009-67-2,5628-72-8,14367-54-5,14367-67-0)

Guidance literature:

With C₄₂H₄₈CoP₂; hydrogen; triethylamine; zinc; In methanol; at 50 ℃; for 16h; under 25858.1 Torr; Reagent/catalyst; Solvent; Temperature; enantioselective reaction;

DOI:10.1021/jacs.9b13876

Reference yield: 97.0%

(2S,4R)-2-trifluoromethyl-3-[(S)-2-methyl-3-phenylpropanoyl]-4-phenyloxazolidine (904296-09-9) → 2-methyl-3-phenylpropionic acid (1009-67-2,5628-72-8,14367-54-5,14367-67-0) + (2S,4R)-2-trifluoromethyl-4-phenyl-1,3-oxazolidine (203176-56-1)

Guidance literature:

(2S,4R)-2-trifluoromethyl-3-[(S)-2-methyl-3-phenylpropanoyl]-4-phenyloxazolidine; With lithium aluminium tetrahydride; In diethyl ether; at -10 ℃; for 0.5h;

With sodium chloride; In diethyl ether; at -10 - 20 ℃;

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; tert-butyl alcohol; at 20 ℃; for 1.2h; Further stages.;

DOI:10.1002/anie.200600738

upstream raw materials:

2-methyl-3-phenylpropanoic acid

ethyl 2-methyl-3-phenylpropionate

2-benzyl-2-methylmalonic acid

methyl 2-methyl-3-phenylpropionate

Downstream raw materials:

methyl (S)-(+)-2-benzylpropionate

methyl 2-methyl-3-phenylpropionate

dexamfetamine

(2S)-2-Methyl-3-phenylpropanoic acid chloride

Refernces

• 1、 Chirik, Paul J.,Shevlin, Michael,Zhong, Hongyu. "Cobalt-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Carboxylic Acids by Homolytic H2 Cleavage". supporting information. . Retrieved 2020/03/13.
• 2、 Mandrelli, Francesca,Blond, Aurélie,James, Thomas,Kim, Hyejin,List, Benjamin. "Deracemizing α-Branched Carboxylic Acids by Catalytic Asymmetric Protonation of Bis-Silyl Ketene Acetals with Water or Methanol". . p. 11479 - 11482. Retrieved 2019/07/18.