Methyl eugenol synthesis
- Product Name:Methyl eugenol
- CAS Number:93-15-2
- Molecular formula:C11H14O2
- Molecular Weight:178.23
Yield:93-15-2 95%
Reaction Conditions:
with potassium carbonate in acetone at 20; for 12 h;
Steps:
2.1.1. Methyl-eugenol (2)
To a solution of the eugenol (1) (4.1 g, 25 mmol) in acetone (25 mL), K2CO3 (10.2 g, 75 mmol) and CH3I (10.5 g, 75 mmol) were added. After 12 h, the reaction mixture was filtered and the solvent was removed to afford product 2 in 95% of yield (4.227 g), brownish oil. IR (KBr, cm-1): 3062, 2908, 2835, 1639, 1591, 1517, 1417, 1261, 1153, 1139, 1029, 995, 914, 850, 765, 740, 707, 650; 1H NMR (400 MHz, CDCl3) δ 3.33 (d, J = 7.02 Hz, 2H, CH2-CH=CH2), 3.86 (s, 3H, -OCH3), 3.85 (s, 3H, -OCH3), 5.07 (m, 2H, CH2-CH=CH2), 5.95 (m, 1H, CH2-CH=CH2), 6.77 (m, 3H, Ar-H3,5,6); 13C NMR (100 MHz, CDCl3) δ 39.61 (CH2-CH=CH2), 55.56 (-OCH3), 55.69 (-OCH3), 111.03 (Ar-C6), 111.62 (Ar-C3), 115.40 (CH2-CH=CH2), 120.21 (Ar-C5), 132.40 (Ar-C4), 137.50 (CH2-CH=CH2), 147.15 (Ar-C1), 148.66 (Ar-C2) ppm.
References:
Da Silva, Rodrigo César;Veiga, Fabiano;Vilela, Fabiana Cardoso;Pereira, André Victor;Da Silva Cunha, Thayssa Tavares;Tesch, Roberta;Viegas, Claudio;Dias, Danielle Ferreira;Giusti-Paiva, Alexandre;Veloso, Marcia Paranho;Fraga, Carlos Alberto Manssour [Letters in drug design and discovery,2019,vol. 16,# 10,p. 1157 - 1166]
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