Dicyclohexylcarbodiimide → 6-[4-(4-Methoxycinnamoyloxy)benzoyloxy]hexyl Methyacrylate

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Reaction Steps

This step involved adding a polymerizable group and the remainder of the spacer group to the compound of Step 3. The compound of Step 3 (25.5 g=85 mmole) was slurried in 800 mL dichloromethane. The compound of Step 1 (15.8 g=85 mmole) was added in one portion, followed by dicyclohexylcarbodiimide (17.5 g=85 mmole) and 4-pyrrolidinopyridine (1.3 g=8.5 mmole). The mixture was stirred at room temperature for 4 hours, and then vacuum filtered. The filtrate was washed with 5% aqueous acetic acid, H2O, 3 portions 5% aqueous Na2CO3, H2O, and then dried over MgSO4 and freed of solvent on a rotary evaporator. The resulting solid was crystallized from low-boiling ligroin via a Soxhlet extractor. Fluffy white crystals, m.p. 65°-67° C. Yield 31.8 g. Elemental Analysis: C27H30O7, mol. wt. 466.5. Anal. Calcd: C, 69.5; H, 6.5, O, 24.0. Found: C, 69.5; H, 6.5; 1H NMR (CDCl3): δ (ppm) 4.4 (4H, m).

Provenance & Evidence