Phenol → (3-Chloropropoxy)benzene

Participants

Reaction Steps

To a suspension of 44 g (0.318 mol) of K2CO3 in 300 ml of acetone, 15 g (0.159 mol) of phenol and 18.9 ml (0.191 mol) of 1-bromo-3-chloropropane are added successively at r.t. under N2 atmosphere. The mixture is refluxed for 6 h and concentrated under reduced pressure. The crude mixture is diluted with cold 1 N aqueous NaOH and extracted with AcOEt. The combined extracts are washed with H2O, dried over MgSO4 and concentrated under reduced pressure to give 26.25 g of (3-chloro-propoxy)benzene (yield 83%); NMR (CDCl3): 2.20–2.27 (m, 2H), 3.75 (t, 2H, J=6.04 Hz), 4.11 (t, 2H, J=6.04 Hz), 6.9–6.97 (m, 3H), 7.25–7.31 (m, 2H).

Provenance & Evidence