Benzene hexane → Methyl 2-methyl-5-nitrobenzyl ether

2-Methyl-5-nitrobenzyl chloride (16.2 g) was dissolved in methanol (180 ml) and then sodium methoxide (5.4 g) was added and the mixture refluxed. The reaction was followed by tlc (75/25 v/v, hexane/benzene) and additional quantities of sodium methoxide added and heating continued until the reaction was complete. Finally, the mixture was cooled and filtered. The filtrate was concentrated in vacuo and the residue taken up in methylene chloride, washed with water, then the organic layer was separated and dried over magnesium sulfate. Removal of the drying agent by filtration and concentration of the filtrate in vacuo left 15.8 g, which was recrystallized from 150 ml of hexane to give 11.5 g of white solid with m.p. 45°-49° C. Another run gave a solid which after recrystallization from hexane gave a solid with m.p. 50-52° C.

1. temperaturethe mixture refluxed
2. additionadded
3. temperatureheating
4. temperatureFinally, the mixture was cooled
5. filtrationfiltered
6. concentrationThe filtrate was concentrated in vacuo
7. washwashed with water
8. customthe organic layer was separated
9. dry with materialdried over magnesium sulfate
10. customRemoval of the drying agent
11. filtrationby filtration and concentration of the filtrate in vacuo
12. waitleft 15.8 g, which
13. customwas recrystallized from 150 ml of hexane

ORDレコード

ord-75a364cb91d94bf2be94922a291c0415

出典データセット

uspto-grants-1978_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04101582