(2R)-2-hydroxy-2-(3-methoxyphenyl)acetic acid

Base Information

• Chemical Name: (2R)-2-hydroxy-2-(3-methoxyphenyl)acetic acid
• CAS No.: 32174-39-3
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.176
• Mol file: 32174-39-3.mol

Synonyms:SCHEMBL503789

Chemical Property of (2R)-2-hydroxy-2-(3-methoxyphenyl)acetic acid

Chemical Property:

• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.05790880
• Heavy Atom Count: 13
• Complexity: 181

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=CC(=C1)C(C(=O)O)O
• Isomeric SMILES: COC1=CC=CC(=C1)[C@H](C(=O)O)O

Technology Process of (2R)-2-hydroxy-2-(3-methoxyphenyl)acetic acid

There total 22 articles about (2R)-2-hydroxy-2-(3-methoxyphenyl)acetic 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-(3-methoxyphenyl)glyoxylic acid (26767-10-2) → (S)-2-hydroxy-2-(3-methoxyphenyl)acetic acid (21150-12-9,32174-39-3,104528-82-7,104596-00-1)

Guidance literature:

With C₄₈H₅₀N₂O₂P₂Ru*2C₁₈H₁₅P*4Cl^(1-)*2Ru⁽²⁺⁾; hydrogen; sodium acetate; triphenylphosphine; In methanol; at 0 ℃; for 24h; under 30003 Torr; enantioselective reaction; Autoclave;

DOI:10.1002/adsc.201700846

Reference yield: 97.0%

→ (S)-2-hydroxy-2-(3-methoxyphenyl)acetic acid (21150-12-9,32174-39-3,104528-82-7,104596-00-1)

Guidance literature:

With potassium tert-butylate; hydrogen; In ethanol; at 20 ℃; for 24h; under 11400.8 Torr; Inert atmosphere; Autoclave;

Reference yield: 67.0%

(S)-(-)-2-hydroxy-2-(3-methoxyphenyl)acetonitrile (10049-65-7,53313-94-3,105307-09-3) → (S)-2-hydroxy-2-(3-methoxyphenyl)acetic acid (21150-12-9,32174-39-3,104528-82-7,104596-00-1)

Guidance literature:

With hydrogenchloride; 1. room temperature, 16 h 2. 60 deg C, 3-8 h;

DOI:10.1016/S0040-4039(00)88777-8

upstream raw materials:

3-methoxy-α-[(trimethylsilyl)oxy]benzeneacetonitrile

chloro-trimethyl-silane

potassium cyanide

3-methoxy-benzaldehyde

Downstream raw materials:

(R)-m-Methoxymandelic acid

(S)-2-hydroxy-2-(3-methoxyphenyl)acetic acid

C₁₁H₁₂O₅

hydroxy-(3-methoxy-phenyl)-acetic acid methyl ester

Refernces

• 1、 Guo, Huan,Li, Jing,Liu, Delong,Zhang, Wanbin. "The Synthesis of Chiral α-Aryl α-Hydroxy Carboxylic Acids via RuPHOX-Ru Catalyzed Asymmetric Hydrogenation". . p. 3665 - 3673. Retrieved 2017/09/11.
• 2、 Coles,Ellis,Leung,Sarson,Threlfall,Tizzard. "Relationships between the racemic structures of substituted mandelic acids containing 8- and 10-membered hydrogen bonded dimer rings". . p. 10816 - 10823. Retrieved 2015/02/19.