Hydrochloric Acid → HCID 20318397, compound

Temperature

68 °C

11.8 grams of 5-tert.-butyl-2,3-dimethyl-4-hydroxyphenylacetic acid was added at 20°C to 200 ml of methanol previously saturated with hydrogen chloride gas. The slightly pinkish solution was heatd at reflux (68°C) for 3 hours after which about one-half of the solvent was removed at reduced pressures and the reaction mixture then poured into about 500 ml of an ice-water mixture with stirring until all the ice had melted. The precipitated crystals were filtered, washed with water and dissolved in benzene. The benzene solution was successively washed with water, saturated sodium bicarbonate solution and finally with water to pH 7, the benzene solution being dried over anhydrous sodium sulfate. The clear benzene solution, freed of drying agent by filtration, was concentrated at reduced pressure. The resulting solid residue was triturated with hexane to remove color bodies. After recrystallization from methanol, the desired product was obtained as white crystals melting at 117° to 119°C (Compound 14).

1. customwas removed at reduced pressures
2. additionthe reaction mixture then poured into about 500 ml of an ice-water mixture
3. filtrationThe precipitated crystals were filtered
4. washwashed with water
5. dissolutiondissolved in benzene
6. washThe benzene solution was successively washed with water, saturated sodium bicarbonate solution and finally with water to pH 7
7. dry with materialthe benzene solution being dried over anhydrous sodium sulfate
8. customof drying agent
9. filtrationby filtration
10. concentrationwas concentrated at reduced pressure
11. customThe resulting solid residue was triturated with hexane
12. customto remove color bodies
13. customAfter recrystallization from methanol

ORD record

ord-0fd0b1d16d19406286788a80bc0dd089

Source dataset

uspto-grants-1976_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03984460