Hydrochloric Acid → HCID 21387664, compound

A mixture of 2-(2-methylbenzyl)furan (5.2 g.), anhydrous sodium carbonate (12.8 g.) and methanol (120 ml.) was stirred at -2° C. during the addition, over 40 minutes, of a solution of bromine (1.6 ml.; 9.3 g.) in methanol (24 ml.). The mixture was stirred for a further 5 minutes, diluted with water (300 ml.) and extracted with toluene (4 × 35 ml.). The combined toluene extracts were dried over magnesium sulphate and evaporated to dryness to give crude 2-(2-methylbenzyl)-2,5-dimethoxy-2,5-dihydrofuran (7.2 g.) in the form of a pale brown coloured oil, which was then heated under reflux with phenol (20 g.) and hydrazine hydrate (2.6 ml.) for 70 hours in an oil bath at 120° C. Hydrochloric acid (100 ml. of 2N and 10 ml. of concentrated hydrochloric acid) was added and the mixture was steam-distilled to remove phenol. The mixture was then cooled and extracted with diethyl ether (50 ml.). The ether solution was extracted with N hydrochloric acid (5 × 10 ml.). Dissolved diethyl ether was removed from the combined aqueous acid extracts by the passage of a stream of air. The aqueous acid solution was then treated with charcoal, filtered, neutralised with solid sodium bicarbonate, basified by the addition of aqueous sodium hydroxide solution (2N; 10 ml.) and extracted with chloroform (5 × 20 ml.). The combined chloroform extracts were washed with water, dried over magnesium sulphate and distilled to give 3-(2-methylbenzyl)pyridazine (2.7 g.) as a white solid, m.p. 86°-89° C. [b.p. 115°-125° C. (bath temperature)/0.1 mm.Hg], the melting point of which was raised to 89°-91° C. by dissolution in 2N hydrochloric acid, filtration and precipitation from the clarified solution by the addition of solid sodium carbonate.

1. extractionextracted with toluene (4 × 35 ml.)
2. dry with materialThe combined toluene extracts were dried over magnesium sulphate
3. customevaporated to dryness
4. customto give crude 2-(2-methylbenzyl)-2,5-dimethoxy-2,5-dihydrofuran (7.2 g.) in the form of a pale brown coloured oil, which
5. temperaturewas then heated
6. distillationthe mixture was steam-distilled
7. customto remove phenol
8. temperatureThe mixture was then cooled
9. extractionextracted with diethyl ether (50 ml.)
10. extractionThe ether solution was extracted with N hydrochloric acid (5 × 10 ml.)
11. customDissolved diethyl ether was removed from the combined aqueous acid extracts by the passage of a stream of air
12. additionThe aqueous acid solution was then treated with charcoal
13. filtrationfiltered
14. additionbasified by the addition of aqueous sodium hydroxide solution (2N; 10 ml.)
15. extractionextracted with chloroform (5 × 20 ml.)
16. washThe combined chloroform extracts were washed with water
17. dry with materialdried over magnesium sulphate
18. distillationdistilled

ORD record

ord-40a7d941ea7146b8bf6cd2558811fbef

Source dataset

uspto-grants-1978_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04067723