Réaction #1552021

Équation de réaction

triglycerol

diglycerol

decanal

→

product

Rendement 15.0%

3-(3-(3-(decyloxy)-2-hydroxypropoxy)-2-hydroxypropoxy)propane-1,2-diol

Rendement 15.0%

Conditions de réaction

Traitement

1. 1
   ExtractionAfter the reaction completion, the product is extracted with diethyl ether (30 mL×7)
2. 2
   AutreThe solvent is evaporated
3. 3
   Autrea half of the crude product is chromatographed on silica gel using straight ethyl acetate
4. 4
   Autresolvent evaporated

Mode opératoire

The procedure of Example 1 is repeated, except 168.2 g (0.70 mol) of triglycerol from Solvay is used in place of diglycerol, 21.88 g (0.14 mol) of decanal is used in place of nonanal, and 1.1 g of 5% Pd/C is used in place of 1.03 g of 5% Pd/C. After the reaction completion, the product is extracted with diethyl ether (30 mL×7). The solvent is evaporated and a half of the crude product is chromatographed on silica gel using straight ethyl acetate. Appropriate fractions are combined, solvent evaporated to give 8.01 g of the product as a mixture of isomers. 1H NMR (δ, CDCl3, ppm): 0.88 t (3 H, CH3), 1.26 (14 H, (CH2)7), 1.58 t (2 H, CH2), 3.4-4.2 m (21 H, triglycerol moiety+CH2O+OH groups). 13C NMR (δ, CDCl3, ppm): 14.44, 23.02, 26.41, 29.64, 29.80, 29.90, 29.93, 32.20, 29.96, 64.15 (decyl), 69.82, 69.88, 71.04, 71.13, 71.99, 72.01, 72.03, 72.06, 73.24, 73.28, 73.32, 73.36 (triglycerol). GS/MS with TMS derivatization: 668 (MW+four TMS groups).

Source