4-Aminophenol → HCID 14500502, compound

A mixture of 30.9 g (0.28 mol) of p-aminophenol in about 300 mL of acetone was stirred in an ice bath and a solution of 25 g (0.14 mol) of 4-bromobutyryl chloride in about 50 mL of acetone was dripped in over 20 minutes. The reaction was stirred cold for another 1/2 hour and then at room temperature for two hours. It was then ice cooled and the mixture filtered. The precipitate was washed with about 200 mL of cold acetone. The filtrate was evaporated and the residue slurried in about 200 mL of 1N HCl, whereupon a precipitate formed. The mixture was ice cooled, filtered, and the precipitate was washed with additional 1N HCl followed by water. The precipitate was dissolved in about 100 mL of ethanol at room temperature, diluted with about 160 mL of water, ice cooled and filtered. The precipitate was washed with a mixture of water and ethanol and then with hexane to yield 18.1 g (52%) of 4-bromo-N-(4-hydroxyphenyl)butanamide, mp 142.5°-144.5° C.

1. customwas dripped in over 20 minutes
2. stirringThe reaction was stirred cold for another 1/2 hour
3. temperatureice cooled
4. filtrationthe mixture filtered
5. washThe precipitate was washed with about 200 mL of cold acetone
6. customThe filtrate was evaporated
7. customformed
8. temperaturecooled
9. filtrationfiltered
10. washthe precipitate was washed with additional 1N HCl
11. dissolutionThe precipitate was dissolved in about 100 mL of ethanol at room temperature
12. additiondiluted with about 160 mL of water, ice
13. temperaturecooled
14. filtrationfiltered
15. washThe precipitate was washed with a mixture of water and ethanol

ORD record

ord-4aff0509a12b491fbe0b8f9a60f1bbc3

Source dataset

uspto-grants-1989_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04835180