(-)-Dibenzoyl-L-tartaric acid monohydrate Chemical Properties

Melting point:

88-89 °C(lit.)

alpha 

-115 º (c=5, ethanol)

refractive index 

-108.5 ° (C=1, EtOH)

storage temp. 

Store below +30°C.

form 

Powder

color 

White

optical activity

[α]20/D 110±3°, c = 5% in ethanol

Water Solubility 

SOLUBLE

BRN 

4065263

InChI

InChI=1/C18H14O8.H2O/c19-15(20)13(25-17(23)11-7-3-1-4-8-11)14(16(21)22)26-18(24)12-9-5-2-6-10-12;/h1-10,13-14H,(H,19,20)(H,21,22);1H2/t13-,14-;/s3

InChIKey

DXDIHODZARUBLA-DTPOWOMPSA-N

SMILES

[C@@H](C(=O)O)(OC(=O)C1C=CC=CC=1)[C@H](C(=O)O)OC(=O)C1C=CC=CC=1.O |&1:0,13,r|

CAS DataBase Reference

62708-56-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

WW8070000

F 

3

TSCA 

Yes

HS Code 

29181990

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2

MSDS

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

(-)-Dibenzoyl-L-tartaric acid monohydrate Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

(-)-Dibenzoyl-L-tartaric acid is used as an intermediate in pharmaceutical and agro chemical industries. It is used as chiral auxiliary in organic synthesis and as a resolution agent in the synthesis of rameleton.

General Description

(-)-O,O′-Dibenzoyl-L-tartaric acid monohydrate may be used as a chiral resolving agent for the resolution of racemic bioactive compounds such as (±)-3-(3-hydroxyphenyl)-N-(1-propyl)-piperidine and (±)-2-(5,6-dimethoxy-1,2,3,4-tetrahydro-1-naphthyl)-imidazoline to isolate the corresponding (-)-enantiomeric forms.

Synthesis

(1) take 1 portion of L-tartaric acid and appropriate amount of organic solvent into the reactor by weight, add 0.1-0.001 portion of catalyst to the reactor under stirring condition, after that, add 1~3 portions of benzoyl chloride to the reactor at a drop acceleration rate of 1-10 mL/min, and then continue the reaction for 4h after the drop is completed, and then, transfer the reaction mixture into a centrifuge for centrifugal separation. Centrifugal separation was carried out to obtain solid L-(-)-dibenzoyltartaric anhydride, standby; said catalyst was copper sulfate or ferrous sulfate;

(2) L-(-)-dibenzoyltartaric anhydride prepared in step (1) was put into the reaction kettle, to which was added an equal weight of toluene and water, and heated and refluxed at 100 ?? for 2-4h, and after that, it cooled down to the ambient temperature, and the resulting mixture was transferred to the centrifuge for the reaction, and then, the mixture was transferred to the centrifuge for the reaction, and then the reaction was continued for 4h. The mixture was transferred to a centrifuge for centrifugal separation to obtain solid L-(-)-dibenzoyltartaric acid.

Purification Methods

Crystallise the acid from water (18g from 400 mL boiling H2O) and stir vigorously while cooling in order to obtain crystals; otherwise an oil will separate which solidifies on cooling. Dry it in a vacuum desiccator over KOH/H2SO4 (yield 16.4g) as monohydrate, m 88-89o. It crystallises from xylene as the anhydrous acid, m 173o (150-153o). It does not crystallise from *C6H6, toluene, *C6H6/pet ether (oil), or CHCl3/pet ether. [Butler & Cretcher J Am Chem Soc 55 2605 1933, Acs et al. Tetrahedron 41 2465 1985, R(+) Beilstein 9 IV 557, S(-) Beilstein 9 III 870.]

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