Synthesis and application transformation of 2-acrylate dodecyl ester

2-dodecyl acrylate, English name Dodecyl acrylate, colorless transparent liquid at room temperature and pressure. Dodecyl 2-acrylate can be used as a synthetic intermediate for organic synthesis, biochemistry and fine chemicals, and can be used for the preparation of drug molecules, pesticide molecules, and bioactive molecules. In addition, dodecyl 2-acrylate can also be used in the production of dyes, adhesives and coatings.
Solubility
Dodecyl 2-acrylate is soluble in common organic solvents such as N, n-dimethylformamide, ethyl acetate, dichloromethane, etc., but dodecyl 2-acrylate is insoluble in water.
Application transformation
The solution of liquid bromine (1.24 mL, 24.2mmol) in CH2Cl2 (20 mL) was slowly added by drip to the cold solution of lauryl acrylate (4.00 mmol) in CH2Cl2 (25 mL), and the reaction mixture was stirred at 0 ° C for 3 hours. At the end of the reaction, the mixture is quenched with Na2S2O3, then the reaction mixture is extracted three times with CH2Cl2, and the combined extract is washed with salt water, and dried on MgSO4, filtered to remove the desiccant and evaporate the solvent. NaN3 (60.6 mmol) was carefully added to the intermediate including dibromide in N, n-dimethylformamide (DMF) (45 ml) solution at 0 ° C. The reaction mixture was stirred at room temperature (23 ° C) for 13 h. The reaction process was monitored by 1H NMR. After the reaction, the reaction mixture was quenched with H2O and extracted with Et2O three times. The two combined extracts were washed with salt water and dried on MgSO4. The volatile substances were removed in vacuum, and then DBU (1, 8-diazecyclododecane 7-ene) (2.46 ml, 15.7 mmol, 1.2 equivalent diazonium) was slowly added to the crude product in Et2O (60 ml) solution at 0℃. The mixture was stirred at 0℃ for 1.5 hours. The mixture was then quenched with H2O, then extracted with ether three times, washed twice with salt water to combine the extract, and dried on MgSO4, filtered to remove the desiccant and evaporate the filtrate solvent, and finally by silica gel column chromatography (silica gel; Hexane: EtOAc=90:10) The target product molecules can be obtained by separating and purifying the residue.
Dodecyl 2-acrylate (1 mmol) and propanal (7 mmol) were slowly added to Pd (OAc) 2 (45 mg, 0.20 mmol, 20 mole %), molybdenum complex (38 mg, 15 micromol) and CeCl3-7H2O (75 mg) in a solution of acetic acid (0.5 ml). 0.20 mmol) in a mixture of methanol (1.0 ml) and acetic acid (4.5 ml), the resulting reaction mixture was stirred at O2 (1 atmospheric pressure) for about 3.5 hours, and then stirred at 70 ° C for a further 4.5 hours. After the reaction, the mixture was analyzed by GLC and GC-MS, the solvent was removed under reduced pressure, sodium bicarbonate was added to the reaction system to neutralize the mixture, and then the mixture was extracted with ethyl ether (50 ml), the resulting organic phase was dried and concentrated, and finally the target product was separated and purified by sphere-to-sphere distillation.
Storage condition
The chemical properties of dodecyl 2-acrylate are relatively stable and will not decompose under normal circumstances, but the double bonds in dodecyl 2-acrylate can be oxidized by oxidants into corresponding epoxides, so dodecyl 2-acrylate needs to be stored in a sealed room temperature and dry environment away from oxidants.