1-Pentanol → 2-Methyl-acrylic acid 6-[4-(2-pentoxycarbonyl-vinyl)-phenoxy]-hexyl ester

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Reaction Steps

To a 250-mL round-bottom flask were added 2-methyl-acrylic acid 6-[4-(2-hydroxycarbonyl-vinyl)-phenoxy]-hexyl ester (4.98 g, 15.0 mmol), 1-pentanol (1.785 mL, 16.5 mmol) and 4-dimethylaminopyridine (DMAP,92 mg, 0.75 mmol) as solids and a stirbar. The flask was purged with N2, followed by the addition of CH2Cl2 (35 mL). The suspension was stirred at room temperature for 20 min to give a white slurry. The flask was cooled in an ice bath and N,N′-dicyclohexylcarbodiimide (DCC, 3.25 g, 15.75 mmol) was introduced. The mixture quickly became a light yellow solution, which was then removed from the ice bath and stirred at room temperature. After 20 h, the resulting white slurry was loaded on a SiO2 column (˜100 g) for quick purification. The product was eluted off with 10% EtOAc in hexanes. The fractions with the desired product were combined, concentrated and then dried in vacuo to a clear oil, which turned into a white solid (Addition Monomer 6) upon cooling (5.45 g, 90%).

Provenance & Evidence