Hydrochloric Acid → 4-Hydroxy-o-toluic acid

Temperature

100 °C

4'-Hydroxy-2'-methylacetophenone (15 gm, 0.1 mol) was dissolved in pyridine and iodine (25.4 gm) was added. This mixture was heated to 100° C. for 1 hr and then allowed to stand at room temperature overnight. A thick precipitate was obtained and the mixture was diluted with Et2O before filtering. The solid so obtained was added to 5N NaOH (200 ml) and heated on the steam bath for 1 hr before being cooled and acidified with HCl. This mixture was extracted twice with Et2O and the pooled organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was crystallized from Et2O-hexane to give 9.8 gm of the title compound as a solid.

1. customA thick precipitate was obtained
2. filtrationbefore filtering
3. customThe solid so obtained
4. temperatureheated on the steam bath for 1 hr
5. temperaturebefore being cooled
6. extractionThis mixture was extracted twice with Et2O
7. washthe pooled organic layers were washed with brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. customevaporated to dryness
11. customThe residue was crystallized from Et2O-hexane

ORD record

ord-0b8061fbc29f44b593d20e2d854fc248

Source dataset

uspto-grants-1993_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05229381