Pyridine → HCID 136062499, compound

Participants

Reaction Conditions

Reaction Steps

In a 250 ml 3-neck round bottom flask equipped with a magnetic stirrer and gas inlet was dissolved 8.21 g (32.0 mmol) 2-((4-(2-hydroxyethyl)phenyl)diazenyl)-4-methylphenol in 200 ml anhydrous THF. ˜50 mg 4-Methoxyphenol (50 mg, Aldrich) was added followed by 20.1 g (254 mmol) anhydrous pyridine. The reaction mixture was cooled to −20° C. and 4.75 g (45.4 mmol) methacryloyl chloride was added dropwise. The reaction mixture was stirred for 1 hour at −20° C. and 20 hours at ambient temperature. The solid was filtered and 200 ml diethyl ether was added to the filtrate. Ethyl acetate (100 ml) was also added to aid in the separation. The organic layer was washed with 0.5 N HCl, and then dried over magnesium sulfate and then filtered. The solvent was removed under removed pressure and the crude product was recrystallized in ethanol to give an orange solid which was rinsed with cold ethanol and dried overnight under high vacuum at room temperature to afford 3.1 g (30%). 1H NMR (CDCl3) delta: 12.67 (s, 1H, Ar—OH), 7.82 (d, 2H, Ar—H), 7.73 (s, 1H, Ar—H), 7.38 (d, 2H, Ar—H), 7.15 (d, 1H, Ar—H), 6.93 (d, 1H, Ar—H), 6.08 (s, 1H, vinyl-H), 5.56 (s, 1H, vinyl-H), 4.41 (m, 2H, CH2OCO), 3.07 (m, 2H, Ar—CH2), 2.38 (s, 3H, Ar—CH3), 1.93 (s, 3H, C═C—CH3).

Provenance & Evidence