Hydrochloric Acid → Hydroxyphenylacetic acid

In an autoclave were placed 0.5 g of p-hydroxy-β,β-dichlorostyrene ##STR12## 1.0 g of sodium hydroxide and 5 ml of methanol. The mixture was heated at 120°-130° C. for 4 hours. Then the methanol was distilled off. To the residue was added 10 ml of water and the mixture was refluxed for 30 minutes. After completion of the reaction, the reaction mixture was acidified by concentrated hydrochloric acid and was extracted three times with 10 ml of ether. The extract was dried over anhydrous magnesium sulfate and the ether was distilled off. The residue was purified by silica gel column chromatography by using benzene, n-hexane and ethyl acetate (10:10:3) as a developer solvent to afford 0.3 g of p-hydroxyphenylacetic acid ##STR13## Yield 94.5%, m.p. 151°-152° C. NMR (CDCl3, δ, ppm) 3.50 (s, 2H), 4.25 (b.s., 2H), 6.92 (m, 4H)

1. temperatureThe mixture was heated at 120°-130° C. for 4 hours
2. distillationThen the methanol was distilled off
3. additionTo the residue was added 10 ml of water
4. temperaturethe mixture was refluxed for 30 minutes
5. customAfter completion of the reaction
6. extractionwas extracted three times with 10 ml of ether
7. dry with materialThe extract was dried over anhydrous magnesium sulfate
8. distillationthe ether was distilled off
9. customThe residue was purified by silica gel column chromatography

ORD record

ord-0b54db041fb94ea8a71afa1474c46191

Source dataset

uspto-grants-1985_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04544766