4-Coumaric acid → 4-Vinylphenol

Temperature

135 °C

In a 1-liter sulfonating flask equipped with mechanical stirrer, reflux condenser and nitrogen delivery line, 300 ml of dimethyl sulfoxide are added to 150 g (0.91 mol) of 4-hydroxycinnamic acid, 6 g (54 mmol) of hydroquinone and 6 g (39 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene. The mixture is then heated at 135° C. for 31/2 hours. After cooling, the mixture is poured onto ice and extracted three times with 500 ml of diethyl ether, and the organic phase is washed five times with 100 ml of water, dried over magnesium sulfate and concentrated. The resulting oil is recrystallised twice from n-hexane to yield 69.07 g (0.58 mol, 63% of the theoretical yield) of 4-hydroxystyrene in the form of a white powder (m.p. 68° C.).

1. customequipped with mechanical stirrer
2. temperaturereflux condenser
3. temperatureAfter cooling
4. additionthe mixture is poured onto ice
5. extractionextracted three times with 500 ml of diethyl ether
6. washthe organic phase is washed five times with 100 ml of water
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated
9. customThe resulting oil is recrystallised twice from n-hexane
10. customto yield 69.07 g (0.58 mol, 63% of the

ORD record

ord-dee086b3dbe7405ca4cdb115ec555481

Source dataset

uspto-grants-1993_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05274060