Hydroxyphenylacetic acid → 3-(3,5-Dimethylphenyl)-2-(4-hydroxyphenyl)-acrylic acid

To a mixture of 43 (3.23 g, 24 mmol), 4-hydroxyphenylacetic acid (3.66 g, 24 mmol) and potassium acetate (2.83 g, 28 mmol) was added acetic anhydride (100 mL). The mixture was heated to reflux for 4 h, cooled to room temperature, and then poured over water (400 mL). After stirring for 1.5 h, a solid gum settled to the bottom and the supernatant was decanted. To the residue was added THF (100 mL) and 1N NaOH (150 mL) and the mixture was stirred for 30 min. The mixture was acidified with 1N HCl (200 mL) and the product was extracted into ethyl acetate (300 mL), washed with water (300 mL), brine (300 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude solid was crystallized in toluene to yield 2.65 g (42%) of a pale yellow solid 44.

1. temperatureThe mixture was heated
2. temperatureto reflux for 4 h
3. customwas decanted
4. additionTo the residue was added THF (100 mL) and 1N NaOH (150 mL)
5. stirringthe mixture was stirred for 30 min
6. extractionthe product was extracted into ethyl acetate (300 mL)
7. washwashed with water (300 mL), brine (300 mL)
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe crude solid was crystallized in toluene

ORD record

ord-c34c998b6ff3423c85140755bb0c70e2

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07407978B2