Methyl (S)-o-Chloromandelate

Base Information

• Chemical Name: Methyl (S)-o-Chloromandelate
• CAS No.: 32345-60-1
• Molecular Formula: C9H9ClO3
• Molecular Weight: 200.622
• DSSTox Substance ID: DTXSID00457939
• Nikkaji Number: J2.761.450G
• Wikidata: Q72452936
• Mol file: 32345-60-1.mol

Synonyms:32345-60-1;Methyl (S)-o-Chloromandelate;2-Chloromandelic Acid Methyl Ester;Methyl 2-Chloro-L-mandelate;(s)-(+)-2-chloromandelic acid methyl ester;(S)-Methyl 2-(2-chlorophenyl)-2-hydroxyacetate;METHYL (2S)-2-(2-CHLOROPHENYL)-2-HYDROXYACETATE;Methyl (S)-2-(2-Chlorophenyl)-2-hydroxyacetate;MFCD02259731;starbld0006394;SCHEMBL3685278;DTXSID00457939;2-Chloro-L-mandelic Acid Methyl Ester;BS-47146;CS-0159370;M2383;E75713;Methyl (S)-2'-Chloro-alpha-hydroxyphenylacetate;J-018710;(S)-2'-Chloro-alpha-hydroxyphenylacetic Acid Methyl Ester;(S)-alpha-Hydroxy-2-chlorobenzeneacetic acid methyl ester

Chemical Property of Methyl (S)-o-Chloromandelate

Chemical Property:

• Refractive Index: 1.5400-1.5440
• Boiling Point: 297.7±25.0 °C(Predicted)
• PKA: 11.82±0.20(Predicted)
• PSA: 46.53000
• Density: 1.316
• LogP: 1.54640
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 200.0240218
• Heavy Atom Count: 13
• Complexity: 184

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-ChloromandelicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C1=CC=CC=C1Cl)O
• Isomeric SMILES: COC(=O)[C@H](C1=CC=CC=C1Cl)O

Technology Process of Methyl (S)-o-Chloromandelate

There total 9 articles about Methyl (S)-o-Chloromandelate 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: 97.0%

methanol (67-56-1) + (S)-2-chloromandelic acid (10421-85-9,52923-23-6,52950-18-2,52950-19-3) → methyl (S)-2-hydroxy-2-(2-chlorophenyl)acetate (32345-60-1)

Guidance literature:

With thionyl chloride; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b00007

Reference yield:

rac-methyl 2-chloromandelate (156276-21-0) → methyl (S)-2-hydroxy-2-(2-chlorophenyl)acetate (32345-60-1) + (S)-2-chloromandelic acid (10421-85-9,52923-23-6,52950-18-2,52950-19-3) + methyl (R)-2-chloromandelate (32345-59-8)

Guidance literature:

With esterase BioH mutant L₁₂₃V/L₁₈₁A/L₂₀₇F of Escherichia coli K₁₂ MG₁₆₅₅; In aq. phosphate buffer; acetonitrile; at 25 ℃; for 16h; pH=7.7; Temperature; pH-value; Reagent/catalyst; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.tetlet.2014.12.139

Reference yield:

methyl 2-chlorobenzoylformate (34966-49-9) → methyl (S)-2-hydroxy-2-(2-chlorophenyl)acetate (32345-60-1) + methyl (R)-2-chloromandelate (32345-59-8)

Guidance literature:

With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; sodium formate; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine; In water; at 40 ℃; for 1h; optical yield given as %ee; Inert atmosphere;

DOI:10.1016/j.jorganchem.2009.02.008

upstream raw materials:

2-chloro-benzaldehyde

(S)-2-(2-chlorophenyl)-2-(trimethylsilyloxy)acetonitrile

methanol

(S)-2-chloromandelic acid

Downstream raw materials:

(S)-(2-chloro-phenyl)-(1-methoxy-1-methyl-ethoxy)-acetic acid methyl ester

(R)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno-[3,2-c]pyridin-5(2H,4H,6H)-yl)acetate

(R)-methyl 2-(2-acetoxy-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(2-chlorophenyl)acetate

Refernces

• 1、 Li, Wanwan,Mao, Qi,Shui, Wenqing,Tian, Sheng,Ye, Na,Zhang, Bingjie. "Identification of Novel 1-O-Substituted Aporphine Analogues as Potent 5-HT2C Receptor Agonists". . p. 549 - 559. Retrieved 2020/03/06.
• 2、 Xu, Hong-Wu,Wu, Li-Huan,Ren, Qiang,Liu, Cui-Yu,Yan, Guan-Qing. "Calcium(II)-mediated resolution of methyl o-chloromandelate with chiral O,O′-dibenzoyltartaric acid in preparative scale". . p. 19 - 22. Retrieved 2018/12/11.