(S)-(+)-O-Acetyl-L-mandelic acid

(S)-(+)-O-Acetyl-L-mandelic acid Property

Melting point:

98-101 °C

Boiling point:

317.8±30.0 °C(Predicted)

alpha 

153 º (c=2 in acetone)

Density 

1.259±0.06 g/cm3(Predicted)

refractive index 

153 ° (C=2, Acetone)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Acetone, Chloroform

form 

Solid

pka

2.76±0.10(Predicted)

color 

White

optical activity

[α]28/D +153°, c = 2 in acetone

BRN 

2694109

InChIKey

YCCSWLJUVZBEAS-VIFPVBQESA-N

LogP

1.780 (est)

CAS DataBase Reference

7322-88-5(CAS DataBase Reference)

Safety

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29181990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

(S)-(+)-O-Acetyl-L-mandelic acid Chemical Properties,Usage,Production

Chemical Properties

(S)-(+)-O-Acetyl-L-mandelic acid is white to light yellow crystal powde

Uses

(S)-(+)-O-Acetyl-L-mandelic acid is an antibacterial used particularly in the treatment of urinary tract infections.

Uses

The (R)- and (S)-isomers are chiral derivatizing agents for NMR determination of enantiomeric purity of α-deuterated carboxylic acids, alcohols, and amines.

Synthesis

Example 1; Preparation of (S)-2-acetoxy-2-phenylacetic acid 1; To a round bottom flask containing mandelic acid (15 g, 111 mmol) was added 100 mL of acetic anhydride. After stirring for 5 min, 10 mL of anhydrous ether and a catalytic amount of DMAP were added sequentially. the reaction mixture was stirred at room temperature for 16 h. The reaction was carried out at room temperature. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure to give an amorphous solid. The solid was dissolved with EtOAc (50 mL) and washed sequentially with 1N HCl (2 x 10 mL), water (2 x 10 mL) and saturated saline (10 mL). The organic phase was dried with anhydrous MgSO4, filtered and concentrated under reduced pressure. Purification by column chromatography with hexane solution of 20% EtOAc as eluent gave the target product (15.8 g, 81 mmol) in 73% yield.The Rf value was 0.54 by TLC (unfolding reagent ratio 1:1 hexane:EtOAc).1H NMR (CDCl3, δ): 11.5 (s, 1H), 7.43 (m, 5H), 5.99 ( s, 1H), 2.20 (s, 3H).

Purification Methods

Recrystallise it from *benzene/hexane or toluene, and it has characteristic NMR and IR spectra. [Pracejus Justus Liebig

References

[1] Tetrahedron Asymmetry, 1999, vol. 10, # 19, p. 3701 - 3718
[2] Patent: US2009/215763, 2009, A1. Location in patent: Page/Page column 11
[3] Patent: US2009/311318, 2009, A1. Location in patent: Page/Page column 11-12