D-(-)-MANDELIC ACID BENZYL ESTER Chemical Properties

Melting point:

104-107 °C(lit.)

Boiling point:

387℃

Density 

1.204

refractive index 

-34 ° (C=1, CH3CN)

Flash point:

163℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMF: 30 mg/ml; DMF:PBS (pH 7.2) (1:2): 0.3 mg/ml; DMSO: 25 mg/ml; Ethanol: 20 mg/ml

pka

12.15±0.20(Predicted)

form 

powder to crystal

color 

White to Almost white

optical activity

[α]25/D 55°, c = 1 in chloroform

CAS DataBase Reference

97415-09-3

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29181990

MSDS

• Language:English Provider:SigmaAldrich

D-(-)-MANDELIC ACID BENZYL ESTER Usage And Synthesis

Description

(R)-benzyl Mandelate is a synthetic intermediate useful for pharmaceutical synthesis.

Uses

Benzyl (R)-(-)-mandelate can be employed as reactant to synthesize:

• (S)-α-Hydroxy-N-(2-phenylethyl)benzenepropanamide (α-hydroxyamides) by enzyme catalyzed amidation reaction.
• Optically pure (R)- monomethyl esters of 3-[(tert-butyldimethylsilyl)oxy]pentanedioic acid, which is employed in the preparation of HMG-CoA reductase inhibitors.
• O-Ibuprofenylmandelic acid via acylation reaction with optically active ibuprofen and subsequent hydrogenation.
• Benzyl (R)-2-fluoro-2-phenylacetate via deoxyfluorination of alcohols using AlkylFluor.

Uses

D-(-)-Mandelic Acid Benzyl Ester is a useful reagent for the preparation of a pharmaceutical composition for treating atopic dermatitis.

Synthesis

(1) Synthesis of benzyl (R)-2-hydroxy-2-phenylacetate (D-2): 85.1 g (559 mmol) of D-mandelic acid, 65 mL (628 mmol) of benzyl alcohol, and 1.01 g (5.35 mmol) of p-toluenesulfonic acid were dissolved in 700 mL of benzene, and the reaction was carried out at reflux for 6.5 hours. Upon completion of the reaction, the reaction mixture was washed with water and subsequently concentrated. The residue was recrystallized by ether to give 123.5 g (R)-benzyl 2-hydroxy-2-phenylacetate (D-2) in 91% yield. The melting point was 103.5°C-105°C. Elemental analysis (C15H14O3) Calculated values (%): C, 74.36; H, 5.82; Measured values (%): C, 74.53; H, 5.90. 1H-NMR (CDCl3-TMS) δ (ppm): 3.44 (d, J = 5.6 Hz, 1H), 5.14 (ABq, isolated, J = 12.3 Hz, 1H). J = 12.3 Hz, 1H), 5.22 (d, J = 5.6 Hz, 1H), 5.24 (ABq, Part B, J = 12.3 Hz, 1H), 7.15-7.50 (m, 10H). [α]D = -55.7 ± 1.0 (CHCl3, c = 1.003%, 24°C).

References

[1] Patent: US5047574, 1991, A

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