(S)-3-(4-Hydroxy-2,6-dimethyl-phenyl)-2-methyl-propionic acid

Base Information

• Chemical Name: (S)-3-(4-Hydroxy-2,6-dimethyl-phenyl)-2-methyl-propionic acid
• CAS No.: 332186-76-2
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.257
• Hs Code.: 2918290000
• DSSTox Substance ID: DTXSID00363728
• Nikkaji Number: J1.486.192K
• Wikidata: Q82147466
• Mol file: 332186-76-2.mol

Synonyms:332186-76-2;(S)-3-(4-Hydroxy-2,6-dimethyl-phenyl)-2-methyl-propionic acid;(S)-3-(4-hydroxy-2,6-dimethylphenyl)-2-methylpropanoic acid;(2S)-3-(4-hydroxy-2,6-dimethylphenyl)-2-methylpropanoic acid;2s-mdp;SCHEMBL6264063;DTXSID00363728;MFCD03426258;CS-0199998;(S)-2,6,alpha-Trimethyl-4-hydroxyhydrocinnamic acid;(2's)-4-hydroxy-2,2',6-trimethyl-benzenepropanoic acid;(S)-3-(4-Hydroxy-2,6-dimethyl-phenyl)-2-methyl-propionicacid;(S)-3-(4-hydroxy-2,6-dimethylphenyl)-2-methylpropanoicacid;(2s)-2-methyl-3-(2,6-dimethyl-4-hydroxy-phenyl)propanoic acid

Chemical Property of (S)-3-(4-Hydroxy-2,6-dimethyl-phenyl)-2-methyl-propionic acid

Chemical Property:

• Vapor Pressure: 1.29E-06mmHg at 25°C
• Boiling Point: 385°C at 760 mmHg
• Flash Point: 200.8°C
• PSA: 57.53000
• Density: 1.148g/cm³
• LogP: 2.27220
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 208.109944368
• Heavy Atom Count: 15
• Complexity: 215

Purity/Quality:

97% ^*data from raw suppliers

(S)-3-(4-Hydroxy-2,6-dimethylphenyl)-2-methylpropanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1CC(C)C(=O)O)C)O
• Isomeric SMILES: CC1=CC(=CC(=C1C[C@H](C)C(=O)O)C)O

Technology Process of (S)-3-(4-Hydroxy-2,6-dimethyl-phenyl)-2-methyl-propionic acid

There total 13 articles about (S)-3-(4-Hydroxy-2,6-dimethyl-phenyl)-2-methyl-propionic 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: 92.0%

2-(4-hydroxy-2,6-dimethylbenzyl)-2-methylmalonic acid (194857-84-6) → 3-(4-hydroxy-2,6-dimethylbenzyl)-2-methylpropionic acid (194857-85-7,332186-76-2)

Guidance literature:

In xylene; for 3h; Heating;

DOI:10.1021/jm9607663

Reference yield:

Boc-[(2S)-Mdp]-OH (332186-75-1) → (2S)-2-methyl-3-(2',6'-dimethyl-4'-hydroxyphenyl)-propionic acid (332186-76-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0960-894X(00)00660-0

Reference yield:

4-iodo-3,5-dimethylphenol (80826-86-4) → (2S)-2-methyl-3-(2',6'-dimethyl-4'-hydroxyphenyl)-propionic acid (332186-76-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / Et₃N; DMAP / H₂O; tetrahydrofuran

2: 61 percent / Pd(OAc)2; Et₃N; (p-MePh)3P / acetonitrile / Heating

3: H₂ / Pd/C / ethyl acetate / 50 °C / 3620.04 Torr

4: 88 percent / 1 N aq. NaOH / tetrahydrofuran

5: Et₃N / diethyl ether / -78 - 0 °C

6: n-BuLi / tetrahydrofuran / -78 - 0 °C

7: 71 percent / NaHMDS / tetrahydrofuran / -78 - -25 °C

8: aq. LiOH; H₂O₂ / tetrahydrofuran

9: TFA / CH₂Cl₂

With dmap; palladium diacetate; lithium hydroxide; sodium hydroxide; n-butyllithium; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; triethylamine; Tri(p-tolyl)phosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile; 2: Heck coupling reaction;

DOI:10.1016/S0960-894X(00)00660-0

upstream raw materials:

2-(4-hydroxy-2,6-dimethylbenzyl)-2-methylmalonic acid

O-ethoxycarbonyl-3,5-dimethyl-4-chloromethylphenol

2-(4-hydroxy-2,6-dimethylbenzyl)-2-methylmalonic acid diethyl ester

Boc-[(2S)-Mdp]-OH