Pyridine → 2-Hydroxy-3-((4-methoxyphenyl)diazenyl)-5-methylbenzyl methacrylate

Participants

Reaction Conditions

Reaction Steps

In a 500 ml round bottom flask equipped with a magnetic stirrer and gas inlet was dissolved 8.75 g (32.1 mmol) of 2-(hydroxymethyl)-6-((4-methoxyphenyl)-diazenyl)-4-methylphenol in 300 ml anhydrous THF. ˜50 mg 4-methoxyphenol (MEHQ) was added followed by 16.5 g (209 mmol) anhydrous pyridine. The reaction mixture was cooled to −20° C. and 4.91 g (47.0 mmol) methacryloyl chloride was added dropwise. The reaction mixture was stirred for 1 hour at −20° C. and then 20 hours at ambient temperature. The solid was filtered and diethyl ether (200 ml) and ethyl acetate (200 ml) were added to the filtrate. The organic layer was washed with 0.5 N HCl, and then dried over magnesium sulfate. The solvent was removed under removed pressure and the crude product was recrystallized in methanol to give an orange solid which was rinsed with cold ethanol and then for 20 hours under vacuum (0.1 mm Hg) at room temperature to afford 7.0 g (64%). 1H NMR (CDCl3) delta: 13.12 (s, 1H, Ar—OH), 7.84 (m, 2H, Ar—H), 7.68 (s, 1H, Ar—H), 7.23 (s, 1H, Ar—H), 7.02 (m, 2H, Ar—H), 6.16 (s, 1H, vinyl-H), 5.58 (s, 1H, vinyl-H), 5.31 (s, 2H, Ar—CH2), 3.89 (s, 3H, CH3O—Ar), 2.38 (s, 3H, Ar—CH3), 1.98 (s, 3H, C═C—CH3).

Provenance & Evidence