Hydrochloric Acid → 4-Chloro-2-methylanisole

Temperature

125 °C

To a suspension of 2-methoxy-5-chlorobenzaldehyde (34.5 g, 0.202 mole) in bis-(2-hydroxyethyl)ether (225 ml) was added hydrazine hydrate (17.7 g, 0.353 mole) and the mixture heated on a 125° C. oil bath for 15 minutes. It was then cooled to 50° C. and powdered potassium hydroxide (15.5 g of 85%, 0.24 mole) added. The mixture was heated on a 165° C. oil bath for 30 minutes. After it had cooled to room temperature it was poured into water (600 ml) and the aqueous solution acidified by addition of 6N HCl. Carbon tetrachloride (4×100 ml) extractions of the acid solution, followed by washing the pooled extracts with brine (1×100 ml), drying (MgSO4) and concentration in vacuo gave a clear viscous oil which crystallized upon addition of a small volume of petroleum ether and chilling in an ice bath. The white crystals were filtered and dried in vacuo. Yield=24.7 g (78 %); m.p. 35°-37° C.

1. temperatureIt was then cooled to 50° C.
2. temperatureThe mixture was heated on a 165° C. oil bath for 30 minutes
3. temperatureAfter it had cooled to room temperature it
4. extractionCarbon tetrachloride (4×100 ml) extractions of the acid solution
5. washby washing the pooled extracts with brine (1×100 ml)
6. customdrying
7. concentration(MgSO4) and concentration in vacuo
8. customgave a clear viscous oil which
9. customcrystallized upon addition of a small volume of petroleum ether
10. temperaturechilling in an ice bath
11. filtrationThe white crystals were filtered
12. customdried in vacuo

ORD record

ord-8e3e43cca0c348a9931018af7295e77f

Source dataset

uspto-grants-1986_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04617312