2-Hydroxy-2-(4-methylphenyl)acetic acid

Base Information

• Chemical Name: 2-Hydroxy-2-(4-methylphenyl)acetic acid
• CAS No.: 18584-20-8
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.177
• Hs Code.: 2918199090
• European Community (EC) Number: 662-983-8
• NSC Number: 126594
• UNII: 2S2B4H5RL9
• Nikkaji Number: J405.822D
• Mol file: 18584-20-8.mol

Synonyms:18584-20-8;2-hydroxy-2-(4-methylphenyl)acetic acid;4-Methylmandelic acid;2-hydroxy-2-(p-tolyl)acetic acid;31284-89-6;p-methylmandelic acid;2S2B4H5RL9;MFCD00961860;NSC-126594;P-methyl mandelic acid;4-Methylmaldelic acid;(R)-(-)-4-Methylmandelic acid;NSC126594;NSC 126594;p-Methyl-mandelic acid;Benzeneacetic acid, alpha-hydroxy-4-methyl-;UNII-2S2B4H5RL9;SCHEMBL245405;4-Methylcarboxy-benzyl alcohol;1-(2-(Phenylamino)phenyl)urea;2-hydroxy-2-p-tolylacetic acid;2-hydroxy-2-(p-tolyl)aceticacid;SFGURAWGCAPHON-UHFFFAOYSA-N;AKOS002676241;AKOS016046698;SS-2000;alpha-Hydroxy-4-methylbenzeneacetic acid;AC-19772;SY287845;CS-0318386;FT-0656178;FT-0681248;F20952;A812982;J-509609;J-509639

Chemical Property of 2-Hydroxy-2-(4-methylphenyl)acetic acid

Chemical Property:

• Vapor Pressure: 4.41E-05mmHg at 25°C
• Melting Point: 145-146 °C
• Boiling Point: 336.4°Cat760mmHg
• PKA: 3.55±0.10(Predicted)
• Flash Point: 171.4°C
• PSA: 57.53000
• Density: 1.264g/cm³
• LogP: 1.11300
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 166.062994177
• Heavy Atom Count: 12
• Complexity: 159

Purity/Quality:

99% ^*data from raw suppliers

4-MethylmandelicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(C(=O)O)O

Technology Process of 2-Hydroxy-2-(4-methylphenyl)acetic acid

There total 74 articles about 2-Hydroxy-2-(4-methylphenyl)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: 98.0%

(4-methylphenyl)(oxo)acetic acid (7163-50-0) → (S)-2-hydroxy-2-(p-tolyl)acetic acid (18584-20-8,31284-89-6,58690-84-9,75172-62-2)

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: 90.0%

N'-(2-Hydroxy-2-p-tolyl-acetyl)-hydrazinecarboxylic acid methyl ester (119105-92-9) → 4-methylmandelic acid (18584-20-8,31284-89-6,58690-84-9,75172-62-2)

Guidance literature:

With sodium hydroxide; In acetonitrile; for 3h; Heating;

DOI:10.1016/S0040-4020(01)86184-6

Reference yield: 85.8%

chloroform (67-66-3,8013-54-5) + 4-methyl-benzaldehyde (104-87-0) → 4-methylmandelic acid (18584-20-8,31284-89-6,58690-84-9,75172-62-2)

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; β‐cyclodextrin; at 50 ℃; for 8h;

DOI:10.1080/00397919408012623

upstream raw materials:

2,2,2-trichloro-1-p-tolyl-ethanol

diethyl 2-hydroxy-2-(4-methylphenyl)propane-1,3-dioate

(4-methylphenyl)(oxo)acetic acid

hydroxy-p-tolyl-acetic acid ethyl ester

Downstream raw materials:

(R)-para-methylmandelic acid

(+)-p-methyl-O-acetylmandelic acid

(-)-p-methylmandelic acid

(4-methylphenyl)(oxo)acetic acid

Refernces

• 1、 Xue, Ya-Ping,Wang, Chuang,Wang, Di-Chen,Liu, Zhi-Qiang,Zheng, Yu-Guo. "Highly Efficient Deracemization of Racemic 2-Hydroxy Acids in a Three-Enzyme Co-Expression System Using a Novel Ketoacid Reductase". . p. 1 - 13. Retrieved 2018/04/26.
• 2、 Potera?a, Marcin,Dranka, Maciej,Borowiecki, Pawe?. "Chemoenzymatic Preparation of Enantiomerically Enriched (R)-(–)-Mandelic Acid Derivatives: Application in the Synthesis of the Active Agent Pemoline". . p. 2290 - 2304. Retrieved 2017/05/01.