ChemicalBook Product Catalog Organic Chemistry Carboxylic acids and derivatives Carboxylic acid esters and derivatives (S)-(+)-Methyl mandelate

(S)-(+)-Methyl mandelate

Product Name(S)-(+)-Methyl mandelate
CAS21210-43-5
MFC9H10O3
MW166.17
EINECS145-896-5
MOL File21210-43-5.mol

Chemical Properties

Melting point	56-58 °C
Boiling point	138 °C / 16mmHg
alpha	142 º (c=2, MeOH)
Density	1.1097 (rough estimate)
refractive index	1.4371 (estimate)
Flash point	>110°C
storage temp.	Sealed in dry,Room Temperature
solubility	Chloroform (Sparingly), Methanol (Sparingly)
form	Solid
pka	12.19±0.20(Predicted)
color	White to Off-White
optical activity	[α]20/D +144°, c = 1 in methanol
BRN	2614741
InChI	1S/C9H10O3/c1-12-9(11)8(10)7-5-3-2-4-6-7/h2-6,8,10H,1H3/t8-/m0/s1
InChIKey	ITATYELQCJRCCK-QMMMGPOBSA-N
SMILES	COC(=O)[C@@H](O)c1ccccc1
CAS DataBase Reference	21210-43-5(CAS DataBase Reference)

Safety Information

Safety Statements	22-24/25
WGK Germany	3
HS Code	29181990
Storage Class	11 - Combustible Solids

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

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.

Uses

Methyl (S)-(+)-Mandelate (cas# 21210-43-5) is a compound useful in organic synthesis.

General Description

Optically active building block.

Synthesis

67-56-1

17199-29-0

21210-43-5

GENERAL METHOD: To a stirred solution of 0.1 mol α-acetoxymandelic acid or α-hydroxymandelic acid dissolved in 200 mL of anhydrous methanol at -30°C was slowly added 8.1 mL (13.05 g, 0.11 mol) of thionyl chloride. The reaction solution was continued to be stirred at -30°C for 15 minutes and then moved to room temperature for 48 hours. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure. The residue was adjusted to pH 9 with NaHCO3 solution and subsequently extracted with ether (5 x 50 mL) and the organic phase was dried with MgSO4. After evaporation of the solvent, the resulting (S)-2-hydroxy-2-phenylacetic acid methyl ester crude was purified by either reduced pressure distillation or petroleum ether-toluene mixed solvent crystallization.

References

[1] Patent: JP2005/120020, 2005, A. Location in patent: Page/Page column 9
[2] Angewandte Chemie, International Edition, 2009, vol. 48, # 25, p. 4605 - 4609
[3] Angewandte Chemie, International Edition, 2014, vol. 53, # 37, p. 9860 - 9864,5
[4] Angewandte Chemie, 2014, vol. 126, # 37, p. 10018 - 10022,5
[5] Chemistry Letters, 1997, # 1, p. 55 - 56

(S)-(+)-Methyl mandelate

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

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