Nitrogen → HCID 21997787, compound

Participants

Reaction Steps

A mixture of 4-acetoxy-2,3,5-trimethyl phenol (0.94 g, 4.82 mmol), dibromoethane (4 mL), potassium carbonate (0.80 g, 1.2 eq), 18-crown-6 (20 mg) in acetonitrile (15 mL) was stirred and heated at reflux under an atmsophere of N2 for 8 days. After this time the mixture was concentrated at reduced pressure and the residue partitioned between CH2Cl2 and 1M HCl. The organic phase was dried, filtered and concentrated at reduced pressure. The residue was purified by flash chromatography (9:1 ethyl acetate, petroleum spirit). The product was obtained as a white solid (34%) and was recrystallised from petroleum spirit as colourless needles, m.p 59-60° C. 1H NMR (CDCl3) δ6.55 (s, 1H), 4.24 (t, J=6.2 Hz, 2H), 3.64 (t, J=6.2 Hz, 2H), 2.32 (s, 3H), 2.16 (s, 3H), 2.11 (s, 3H), 2.05 (s, 3H).

Provenance & Evidence