Methylparaben → HCID 43532221, compound

Participants

Reaction Conditions

Reaction Steps

4-Hydroxy-benzoic acid methyl ester (1.52 g, 10 mmol), 5-chloro-1-pentanol (1.22 g, 10 mmol) and triphenylphosphine (2.62 g, 10 mmol) are dissolved in dry THF (30 mL) and cooled to 0° C. Diethylazodicarboxylate (DEAD) (1.74 g, 10 mmol) is dropped into this mixture at 0° C. and stirred at room temperature for 3 days. The reaction mixture is washed with brine, dried over Na2SO4, filtered and evaporated. The crude product is purified using silica-gel column chromatography (CH2Cl2 only to CH2Cl2:2 M NH3 in MeOH=20:1) to give the desired product (1.14 g, 45%). NMR (CDCl3): δ 7.98 (d, 2H, J=8.8 Hz), 6.89 (d, 2H, J=8.8 Hz), 4.02 (t, 2H, J=6.5 Hz), 3.88 (s, 3H), 3.57 (t, 2H, J=6.7 Hz), 1.85 (m, 4H), 1.64 (m, 2H).

Provenance & Evidence