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 1N 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