Ethylparaben → Ethyl 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoate

Participants

Reaction Steps

A solution of 116 mg (0.5 mmol) of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoic acid, 58 mg (0.5 mmol) of ethyl 4-hydroxybenzoate, 117 mg (0.56 mmol) of 1,3-dicyclohexylcarbodiimide and 30 mg (0.25 mmol) of 4-dimethylaminopyridine in 15 ml of methylene chloride was stirred at room temperature for 12 hours. The reaction mixture was then filtered and the filtrate concentrated in-vacuo. The resultant residue was purified by flash chromatography (silica; 5% ethyl acetate in hexanes) to give the title compound as white crystals. PMR (CDCl3): δ 1.32 (6H, s), 1.36 (6H, s), 1.42 (3H, t, J~7.0 Hz), 1.73 (4H, s), 4.40 (2H, q, J~7.0 Hz), 7.28 (2H, d, J~8.1 Hz), 7.45 (1H, d, J~8.8 Hz), 7.93 (1H, dd, J~8.8 Hz, 1.8 Hz), 8.13 (2H, d, J~8.1 Hz), 8.14 (1H, s).

Provenance & Evidence