Chelidonic acid synthesis
- Product Name:Chelidonic acid
- CAS Number:99-32-1
- Molecular formula:C7H4O6
- Molecular Weight:184.1
Yield:99-32-1 46%
Reaction Conditions:
Stage #1:oxalic acid diethyl ester;acetone with sodium ethanolate in ethanol at 60; for 15 h;
Stage #2: with hydrogenchloride;water in ethanol for 44 h;
Steps:
13 4.1.2.11 Chelidonic acid (4-oxo-4H-pyran-2,6-dicarboxylic acid) (12)
Chelidonic acid was synthesized using an adapted literature protocol.33 In a typical experiment, EtONa (69.4 g, 1.02 mol) was suspended in ethanol (300 mL). After 45 min at 60°C, a solution of dry acetone (29 g, 38 mL, 0.5 mol) and diethyl oxalate (155 g, 144 mL, 1.06 mol) was added over a period of 1 h. After the addition was complete, the solution was maintained at 60°C and stirred for an additional 14 h. Then, 230 mL of HCl (37% aqueous solution) and 100 mL of water were added and the mixture was stirred for 1 day. After 24 h, about half of aqueous ethanol was removed under reduced pressure then 300 mL of water and 60mL of HCl (37% aqueous solution) were added to this mixture and stirring was continued for 20 h at 50°C. The resulting solid was filtered off, washed first with water then with acetone before recrystallization from boiling water using charcoal. The filtrate was left at room temperature until formation of crystals. The white crystals were collected and dried under vacuum to give the desired compound 12 (42.3 g, 46%).
References:
Gracia, Stéphanie;Arrachart, Guilhem;Marie, Cécile;Chapron, Simon;Miguirditchian, Manuel;Pellet-Rostaing, Stéphane [Tetrahedron,2015,vol. 71,# 33,p. 5321 - 5336]
68854-18-2
16 suppliers
$189.00/250mg
99-32-1
185 suppliers
$9.00/250mg
105-50-0
395 suppliers
$6.00/5g
99-32-1
185 suppliers
$9.00/250mg
7647-01-0
11 suppliers
$10.00/10g
68854-18-2
16 suppliers
$189.00/250mg
99-32-1
185 suppliers
$9.00/250mg