(S)-(+)-Methyl mandelate

Base Information

• Chemical Name: (S)-(+)-Methyl mandelate
• CAS No.: 21210-43-5
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Hs Code.: 29181990
• Mol file: 21210-43-5.mol

Synonyms:Benzeneaceticacid, a-hydroxy-, methyl ester, (S)-;Mandelic acid, methyl ester, (S)- (8CI);(+)-Mandelic acid methyl ester;(+)-Methyl mandelate;(S)-(+)-Mandelic acid methyl ester;(S)-Methyl mandelate;L-(+)-Mandelic acid methyl ester;Methyl(S)-2-hydroxy-2-phenylacetate;Methyl (S)-a-hydroxybenzeneacetate;Methyl L-mandelate;

Chemical Property of (S)-(+)-Methyl mandelate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.00715mmHg at 25°C
• Melting Point: 56-58 °C
• 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: 1.182 g/cm³
• LogP: 0.89300
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Sparingly)

Purity/Quality:

99% ^*data from raw suppliers

Methyl (S)-(+)-mandelate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl (S)-(+)-Mandelate (cas# 21210-43-5) is a compound useful in organic synthesis. Methyl (S)-(+)-mandelate may be used in the preparation of (S)-(-)2-hydroxy-1,2,2-triphenylethyl acetate and (α′S)-α′-methoxycarbonylbenzyl (2S,4R)-(+)-1,2,4,5-tetrahydro-4-methyl-7,8-methylenedioxy-5-oxo-3-benzothiepin-2-carboxylate.

Technology Process of (S)-(+)-Methyl mandelate

There total 102 articles about (S)-(+)-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: 98.6%

methanol (67-56-1) + (S)-Mandelic acid (17199-29-0) → (S)-Methyl mandelate (21210-43-5)

Guidance literature:

sulfuric acid; for 2h; Heating / reflux;

Reference yield: 98.0%

methyl 2-oxo-2-phenylacetate (15206-55-0) → (S)-Methyl mandelate (21210-43-5) + (R)-methyl mandelate (20698-91-3)

Guidance literature:

With formic acid*triethylamine; Ru/(S,S)-DPEN/MCF; In isopropyl alcohol; at 20 ℃; for 12h;

DOI:10.1039/b615564b

Reference yield: 90.0%

(S)-Mandelic acid (17199-29-0) + 2,2-dimethoxy-propane (77-76-9) → (S)-Methyl mandelate (21210-43-5)

Guidance literature:

With hydrogen cation;

DOI:10.1021/ja00279a059

upstream raw materials:

methanol

phenylglyoxal hydrate

(S)-Mandelic acid

2-[methyl-((S)-1-methyl-2-phenyl-ethyl)-amino]-ethanethiol

Downstream raw materials:

(S)-methyl mandelyl tetrahydropyranyl ether

(S)-methyl mandelyl tetrahydropyranyl ether

(S)-(+)-methyl 2-phenyl-2-(tetrahydropyranyloxy)acetate

4-Methyl-pentanoic acid (S)-methoxycarbonyl-phenyl-methyl ester

Refernces

• 1、 Dakin, Les A.,Schaus, Scott E.,Jacobsen, Eric N.,Panek, James S.. "Carbenoid insertions into the silicon-hydrogen bond catalyzed by chiral copper (I) Schiff base complexes". . p. 8947 - 8950. Retrieved 1998.
• 2、 Lizzadro, Luca,Spie?, Oliver,Schinzer, Dieter. "Total Synthesis of (-)-Disorazole C1". supporting information. p. 4543 - 4547. Retrieved 2021/06/28.
• 3、 de Gonzalo, Gonzalo. "Biocatalysed reductions of α-ketoesters employing CyreneTM as cosolvent". . . Retrieved 2021/02/26.