Methylparaben → Methyl 4-(dodecyloxy)benzoate

Participants

Reaction Steps

Methyl 4-(dec-9-enyloxy)benzoate (3). Synthesized as described above for compound 1. Quantities: K2CO3 (18.2 g, 0.13 mol), methyl-4-hydroxy-benzoate (6.30 g, 41.4 mmol), 10-bromo-1-decene (8.6 mL, 42.8 mmol). Yield 12.0 g (quant.). 1H NMR: δH (CDCl3; 300 MHz): 1.23-1.51 (10 H, m, CH2), 1.77 (2 H, m, O—CH2—CH2), 2.03 (2 H, m, CH2═CH—CH2), 3.85 (3 H, s, OCH3), 3.95 (2 H, t, 3J=6.5 Hz, O—CH2), 4.95 (2 H, m, CH2═CH), 5.79 (1 H, m, CH2═CH), 6.87 (2 H, d, 3J=9.0 Hz, Ar—H), 7.98 (2 H, d, 3J=9.0 Hz, Ar—H). 13C NMR: δC (CDCl3; 75 MHz): 26.0, 28.9, 29.0, 29.1, 29.3, 29.4, 51.7, 68.1, 114.0, 114.2, 122.3, 131.5, 139.0, 162.9, 166.7.

Provenance & Evidence