Sodium Hydroxide → 2,3-Dihydroxybutanedioic Acid

HRID 1606657Notes

Reaction equation

HRID 1606657 reaction equation
[C:1]([OH:10])(=[O:9])[C@H:2]([C@@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[C@H:11]([OH:20])([C:17]([OH:19])=[O:18])[C@H:12]([OH:16])[C:13]([OH:15])=[O:14].[OH-].[Na+]>O>[C:1]([OH:10])(=[O:9])[C@H:2]([C@@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[C:17]([OH:19])(=[O:18])[CH:11]([CH:12]([C:13]([OH:15])=[O:14])[OH:16])[OH:20].[C@H:2]([OH:3])([C:1]([OH:10])=[O:9])[C@H:4]([OH:5])[C:6]([OH:8])=[O:7]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 439655D-Tartaric acid2×HCID 447315Meso-Tartaric acid

Product 3

HCID 8752,3-Dihydroxybutanedioic AcidHCID 439655D-Tartaric acidHCID 447315Meso-Tartaric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a test tube were charged 3.40 g of D-tartaric acid, 1.46 g of meso-tartaric acid, 7.78 g of sodium hydroxide and 10.6 g of water. Following the process of Reference Example 1, the racemization of D-tartaric acid was conducted and the reaction mixture was analyzed to give 0.08 g of unreacted D-tartaric acid, 2.62 g of DL-tartaric acid and 1.72 g of meso-tartaric acid. The conversion of D-tartaric acid to DL-tartaric acid was 77.1%.

Sources & evidence

ORD record
ord-0b823c2d166e4f918c674d53ea1a3e48
Source dataset
uspto-grants-1976_04
Patent number
US03953504

Reaction notes

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