Water → HCID 53741601, compound

Participants

Reaction Steps

To a solution of 3-chloro-5-(3-hydroxypropyl)-6-methoxalylmethylnitrobenzene (19.91 g, 0.063 mol) in acetone (300 mL) was added dropwise a mixture of 20% TiCl3 (340 g, 0.441 mol), water (300 mL), and acetone (300 mL) at room temperature over a period of 30 min. The mixture was stirred for 30 min at room temperature and extracted with AcOEt. The extracts were washed with brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography with 4:1 to 1:2 hexane/toluene to give 11.39 g of the title compound (68%): 1H NMR (CDCl3) δ8.96 (bs, 1H), 7.27 (s, 1H), 7.26 (d, 1H, J=1.7 Hz), 6.97 (d, 1H, J=1.7 Hz), 3.95 (s, 3H), 3.71 (t, 2H, J=6.3 Hz), 2.98 (t, 2H, J=7.8 Hz), 2.00 (m, 2H).

Provenance & Evidence