Ethylparaben → Ethyl4-(8,8-dimethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoate

Participants

Reaction Steps

A solution of 220.7 mg (1.0804 mmol) of 8,8-dimethyl-5,6,7,8-tetrahydro-2-naphthoic acid, 180.6 mg (1.0868 mmol) of ethyl 4-hydroxybenzoate, 227.3 mg (1.1034 mmol) of 1,3-dicyclohexylcarbodiimide and 22.9 mg (0.1874 mmol) of 4-dimethylaminopyridine in 15 ml of methylene chloride was stirred at room temperature for 18 h. The reaction mixture was then filtered and the residue washed with 10 ml of methylene chloride. The filtrate was concentrated in-vacuo and the resultant crude product purified by flash chromatography (silica; 5% ethyl acetate in hexanes) to give the title compound as a colorless oil. PMR (CDCl3): δ 1.35 (6H, s), 1.42 (3H, t, J~7.2 Hz), 1.68-1.76 (2H, m), 1.80-1.92 (2H, m), 2.85 (2H, t, J~6.1 Hz), 4.40 (2H, q, J~7.2 Hz), 7.18 (1H, d, J~ 8.0 Hz), 7.31 (2H, d, J~8.7 Hz), 7.89 (1H, dd, J~8.0 Hz, 1.6 Hz), 8.11-8.22 (3H, m).

Provenance & Evidence