Tri(acetoacetic acid)1,2,3-propanetriyl ester synthesis
- Product Name:Tri(acetoacetic acid)1,2,3-propanetriyl ester
- CAS Number:6079-98-7
- Molecular formula:C15H20O9
- Molecular Weight:344.31
Yield:6079-98-7 400 g
Reaction Conditions:
at 95 - 100; for 2.5 h;Inert atmosphere;Large scale;
Steps:
1 Example 1 - Synthesis of glycerol tris-acetoacetate of formula (IV)
Glycerin (150 g, 1.69 mol), tert-butyl acetoacetate (1350 g, 8.55 mol) are added to a 3000 ml flask in inert atmosphere and the mixture is heated at 95- 100°C for 2.5 hours. The reaction mixture is then concentrated at a reduced pressure of 200-250 mbar and at an internal temperature of 80-90°C, integrating toluene in portions to the reaction mixture for a total of 1.5 1. The end of distillation residue is then cooled at 0-10°C and diluted with isopropanol cooled at -10°C (2.5 1), the phases are separated, discarding the alcoholic phase and obtaining a crude oil (620 g) which is repeatedly washed with cold isopropanol until a product (400 g) is obtained with an HPLC purity (200 nm) in A% of 98.6% with a glycerol bis-acetoacetate content lower than 0.3% and a yield of 70%. 1H-NMR (CDCI3, 300 MHz) δ: 11.8* (s, 1H); 5.34 (m, 1H); 4.99* (s, 1H); 4.32 (m, 4H); 3.49 (s, 6H); 2.25 (s, 9H); 1.96* (s, 3H). *Keto-enol isomerism. HPLC-MS: 345 (M/z+1)
References:
WO2021/70208,2021,A1 Location in patent:Page/Page column 13
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