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

A mixture of the compound from Step 1 (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 combined organic layers were washed with water (4×200 ml), dried over Na2SO4, the solvents were removed by evaporation and the residue was dissolved in 10% HCl/methanol (500 ml). After 10 hours at room temperature the volatile components were removed by evaporation in vacuo. The resulting residue was triturated with hexane to yield the title compound, m.p. 115°-116°.

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

ORD record

ord-7b7e5e9edcee410583c9646daf1f50b7

Source dataset

uspto-grants-1988_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04761425