(S)-(+)-Methyl mandelate 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

InChIKey

ITATYELQCJRCCK-QMMMGPOBSA-N

CAS DataBase Reference

21210-43-5(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29181990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

(S)-(+)-Methyl mandelate Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

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

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.

General Description

Optically active building block.

Synthesis

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

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