Dodecyl gallate synthesis
- Product Name:Dodecyl gallate
- CAS Number:1166-52-5
- Molecular formula:C19H30O5
- Molecular Weight:338.44
Yield:1166-52-5 82%
Reaction Conditions:
with sulfuric acid at 100; for 0.833333 h;Microwave irradiation;
Steps:
4.1.1. Microwave assisted conditions for the synthesis of alkyl gallates 2-7
General procedure: A microwave vial was loaded with gallic acid 1 (0.3mmol, 50mg), the corresponding alcohol (0.9mmol), and concentrated H2SO4 (0.07mL). The reaction vessel was sealed and irradiated in a microwave reactor at 100°C for 50min. After cooling, volatiles were evaporated to dryness and the residue was dissolved in ethyl acetate (30mL) and washed successively with saturated solutions of NaHCO3 (3×20mL) and NaCl (1×20mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was then purified by column chromatography using hexane/EtOAc, (3:7) as the eluent. Melting points and characterization of compounds 2-7 were consistent with those found in the literature [25d]. In our case, the following yields were obtained: 2 (70%), 3 (97%), 4 (83%), 5 (98%), 6 (96%), 7 (82%).
References:
Rivero-Buceta, Eva;Carrero, Paula;Doyagüez, Elisa G.;Madrona, Andrés;Quesada, Ernesto;Camarasa, María José;Peréz-Pérez, María Jesús;Leyssen, Pieter;Paeshuyse, Jan;Balzarini, Jan;Neyts, Johan;San-Félix, Ana [European Journal of Medicinal Chemistry,2015,vol. 92,p. 656 - 671]
1063201-08-0
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