4-Methoxyphenol → 2-((2-Hydroxy-3-((4-methoxyphenyl)diazenyl)-5-methylbenzyloxy)-carbonylamino)ethyl methacrylate

Participants

Reaction Conditions

Reaction Steps

In a 500 ml 3-neck round bottom flask equipped with a magnetic stirrer and nitrogen inlet was dissolved 5.01 g (18.4 mmol) 2-(hydroxymethyl)-6-((4-methoxyphenyl)diazenyl)-4-methylphenol from Example 2 in 300 ml anhydrous THF. Stannous octoate (50 mg, Pfaltz & Bauer) was added followed by 2-isocyanatoethyl methacrylate (3.14 g, 20.2 mmol). MEHQ (100 mg) was added. The reaction mixture was stirred for 20 hr at 60° C. and then poured into 200 ml diethyl ether, and washed with 0.5 N HCl and water. The organic layer was dried with magnesium sulfate, filtered, and rotovapped to give the desired product which was recrystallized in ethanol to give 6.0 g (76%) of an orange solid. 1H NMR (CDCl3) delta: 13.22 (s, 1H, Ar—OH), 7.85 (m, 2H, Ar—H), 7.69 (s, 1H, Ar—H), 7.23 (s, 1H, Ar—HI), 7.03 (m, 2H, Ar—H), 6.09 (s, 1H, vinyl-H), 5.57 (s, 1H, vinyl-H), 5.24 (s, 2H, Ar—CH2), 5.02 (s, 1H, CONH), 4.24 (m, 2H, CH2OCO), 3.90 (s, 3H, Ar—OCH3), 3.53 (m, 2H, OCNHCH2), 2.38 (s, 3H, Ar—CH3), 1.92 (s, 3H, CH3—C═C).

Provenance & Evidence