Water → HCID 18984733, compound

Participants

Reaction Steps

To a solution of 2-(3-hydroxypropyl)-4-chloro-toluene (6.2 g, 33.5 mmol) and triethylamine (9.34 mL, 67 mmol) in dichloromethane (25 mL) was added acetic anhydride (5.1 mL, 50.3 mmol) at room temperature. The mixture was stirred for 2 h and concentrated in vacuo. The residue was diluted with aq. KHSO4 and extracted with AcOEt. The extracts were dried and concentrated. The residue was dissolved in dichloromethane (50 mL). NO2 +BF4- (5.77 g, 36.85 mmol) was added at 0° C. The mixture was stirred for 30 min at 0° C. and poured into water. The mixture was extracted with AcOEt and the extracts was dried and concentrated. The residue was purified by silica gel column chromatography with 5:1 hexane/AcOEt to give 5.0 g of the title compound: 1H NMR (CDCl3) δ7.63 (bs, 1H), 7.36 (bs, 1H), 4.13 (t, 2H, J=7.2 Hz), 2.78 (t, 2H, J=7.2 Hz), 2.41 (s, 3H), 2.09 (s, 3H), 1.89~2.01 (m, 2H).

Provenance & Evidence