Acetic Acid → Methyl 4-oxo-4-(4-hydroxyphenyl)butanoate

A mixture of the compound from Step A (77.3 g), 48% HBr (310 ml), and acetic acid (620 ml) was heated under reflux for 18 hours. The resulting mixture was cooled to room temperature and poured into 3 liters of water. The resulting solution was extracted with ethyl acetate (3×500 ml). The 200 ml), dried over Na2SO4, the solvents were removed by evaporation and the residue was dissolved in 10% HCl/methanol (500 ml). After 1 hour at room temperature the volatile components were removed by evaporation in vacuo. The resulting residue was triturated with hexane to yield the title compound, mp 115°-116°.

1. temperaturewas heated
2. temperatureunder reflux for 18 hours
3. extractionThe resulting solution was extracted with ethyl acetate (3×500 ml)
4. dry with materialThe 200 ml), dried over Na2SO4
5. customthe solvents were removed by evaporation
6. dissolutionthe residue was dissolved in 10% HCl/methanol (500 ml)
7. customAfter 1 hour at room temperature the volatile components were removed by evaporation in vacuo
8. customThe resulting residue was triturated with hexane

ORD record

ord-2f6abe817e4e48a2888794c91edf2cae

Source dataset

uspto-grants-1992_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05135940