Methyl mandelate

Base Information

• Chemical Name: Methyl mandelate
• CAS No.: 4358-87-6
• Deprecated CAS: 771-90-4
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Hs Code.: 29181980
• European Community (EC) Number: 224-434-7,212-240-5
• NSC Number: 6539
• DSSTox Substance ID: DTXSID30871907
• Nikkaji Number: J60.936F
• Wikidata: Q72492488
• ChEMBL ID: CHEMBL3039009
• Mol file: 4358-87-6.mol

Synonyms:methyl mandelate;methyl mandelic acid

Chemical Property of Methyl mandelate

Chemical Property:

• Appearance/Colour: white to slightly yellow crystals, crystalline
• Vapor Pressure: 0.00715mmHg at 25°C
• Melting Point: 54-56 °C(lit.)
• Refractive Index: 1.535
• Boiling Point: 258.1 °C at 760 mmHg
• PKA: 12.19±0.20(Predicted)
• Flash Point: 113.1 °C
• PSA: 46.53000
• Density: 1.183 g/cm³
• LogP: 0.89300
• Storage Temp.: -20°C
• Solubility.: methanol: 0.1 g/mL, clear
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 166.062994177
• Heavy Atom Count: 12
• Complexity: 150

Purity/Quality:

99% ^*data from raw suppliers

Methyl DL-Mandelate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C(C1=CC=CC=C1)O
• Uses: Methyl DL-Mandelate is a substrate for lipase B from Candida antarctica.

Technology Process of Methyl mandelate

There total 187 articles about Methyl mandelate 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: 74.0%

MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2) + methyl salicylate (119-36-8,8024-54-2) → (RS)-methyl mandelate (4358-87-6) + salicylic acid (69-72-7,25496-36-0,8052-31-1)

Guidance literature:

MANDELIC ACID; With potassium carbonate; In N,N-dimethyl acetamide; at 110 ℃; for 0.5h;

methyl salicylate; at 110 ℃; for 24h;

DOI:10.1055/s-0033-1340285

Reference yield: 65.0%

methyl 2-oxo-2-phenylacetate (15206-55-0) → (RS)-methyl mandelate (4358-87-6) + benzaldehyde (100-52-7)

Guidance literature:

With potassium tetracarbonylhydridoferrate; In methanol; at 50 ℃; for 4h;

DOI:10.1016/S0040-4039(00)78502-9

Reference yield: 62.1%

phenylacetaldehyde (122-78-1) → (RS)-methyl mandelate (4358-87-6) + benzaldehyde (100-52-7) + Benzoylformic acid (611-73-4) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With pyridine; water; oxygen; triethylamine; pyridine; compound with copper (II)-nitrate; In methanol; at 25 ℃; for 12h; under 1748 Torr; Further byproducts given. Title compound not separated from byproducts;

DOI:10.1021/jo00297a013

upstream raw materials:

methanol

MANDELIC ACID

phenylglyoxal hydrate

2-(diethylamine)ethanethiol

Downstream raw materials:

1,1,2-triphenyl-1,2-ethanediol

methyl 2-oxo-2-phenylacetate

methyl 2-chloro-2-phenylethanoate

(RS)-mandelamide

Refernces

• 1、 Boyer, Stephen K.,Bach, Joseph,McKenna, Joseph,Jagdmann, Erick. "Mild Hydrogen-Transfer Reductions Using Sodium Hypophosphite". . p. 3408 - 3411. Retrieved 1985.
• 2、 Zhao, Wei,Yan, Patrick K.,Radosevich, Alexander T.. "A phosphetane catalyzes deoxygenative condensation of α-keto esters and carboxylic acids via PIII/PV=O redox cycling". . p. 616 - 619. Retrieved 2015.
• 3、 Dalla,Catteau,Pale. "Mechanistic rationale for the NaBH4 reduction of α-keto esters". . p. 5193 - 5196. Retrieved 1999.
• 4、 Li, Xinying,Mi, Tongge,Guo, Wenjing,Ruan, Zhongrui,Guo, Yu,Ma, Yan-Na,Chen, Xuenian. "KB3H8: An environment-friendly reagent for the selective reduction of aldehydes and ketones to alcohols". . p. 12776 - 12779. Retrieved 2021/12/10.
• 5、 Hou, Shuaitao,Xie, Dewen,Yang, Jingxin,Niu, Xue,Hu, Deyu,Wu, Zhibing. "Design, synthesis and antifungal evaluation of novel mandelic acid derivatives containing a 1,3,4-oxadiazothioether moiety". . p. 166 - 174. Retrieved 2021/05/29.