Ethylparaben → HCID 11058114, compound

Participants

Reaction Steps

Sodium hydride (1.55 g, 61 mmol) was suspended in DMF (150 mL) under an atmosphere of nitrogen. Ethyl-4-hydroxybenzoate (11) (5.06 g, 30 mmol) was added as a solution in DMF (30 mL) via syringe which was then washed with DMF (2×5 mL). The reaction mixture was then stirred at room temperature under an atmosphere of nitrogen for 2 hours. After this time, 1,10-dibromodecane (30.84 g, 103 mmol) was added as a solution in DMF (50 mL) via syringe which was then washed with DMF (2×5 mL). The reaction mixture was then stirred at room temperature under nitrogen for 19 hours. The reaction was quenched with water (200 mL) and the organic fragments extracted with diethyl ether (4×150 mL), dried over MgSO4, and excess solvent removed in vacuo to form a colorless oil. This was purified by flash column chromatography using CH2Cl2/hexane (1:1) to CH2Cl2/hexane (3:1) as eluting solvents to form a white crystalline solid. This was recrystallized from ethanol to form 4-(10-bromo-decyloxy)-benzoic acid ethyl ester (7.38 g, 19.1 mmol, 63%). Rf 0.65 (CH2Cl2), mp 41-42° C. FTIR, νmax/cm−1 1 3023, 2927, 2855, 1708, 1604, 1509, 1468, 1390, 1367, 1312, 1252, 1155, 1018, 851, 772. 1H NMR (CDCl3, 250 MHz), δ/ppm 7.96 and 6.87 (both 2 H, m, Ar—H); 4.32 (2 H, q, 3J=7.1 Hz, −CH2CH3); 3.97 (2 H, t, 3J=6.5 Hz, —OCH2—); 3.38 (2 H, t, 3J=6.9 Hz, —CH2Br); 1.80 (4 H, m, —OCH2CH2— and —CH2CH2Br); 1.42-1.27 (15 H, m, alkyl C—H). 13C{1H} NMR (CDCl3, 63 MHz), δ/ppm 166.2 (C=O); 152.6 and 122.4 (quat. Ar C); 131.3 and 113.8 (Ar C—H); 67.9 and 60.4 (—OCH2—); 33.9, 32.6, 29.2, 29.1, 29.0, 28.9, 28.5, 28.0, 25.8 (CH2); 14.2 (—CH3) λmax/nm (ε/dm3mol−1cm−1) 257 (24641). HRMS (FAB), M+/z C19H30BrO3 (MH+) requires 385.1378, found 385.1374.

Provenance & Evidence