Chloromethyl Methyl Ether → HCID 18461299, compound

To 20 ml of an anhydrous tetrahydrofuran suspension containing 1.78 g of sodium hydride (55% by weight), 30 ml of a solution of 8.02 g of 3-chloro-2,6-dimethyl-4-pivaloyloxyphenol in anhydrous tetrahydrofuran were added dropwise, followed by stirring at room temperature for 30 minutes. To the reaction mixture, 3.28 g of chloromethyl methyl ether were added and the mixture was stirred at room temperature for 13 hours. The reaction mixture was then concentrated by evaporation. Water was added to the concentrate, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. In 30 ml of methanol, 9.30 g of the residue were dissolved. To the resulting solution, 30 ml of a solution of 3.51 g of potassium hydroxide in methanol were added dropwise, followed by stirring at room temperature for 30 minutes. The reaction mixture was concentrated by evaporation. The concentrate was neutralized with 3N hydrochloric acid and sodium bicarbonate, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was separated and purified by chromatography through a silica gel column (eluting solvent: n-hexane/ethyl acetate=10/1), whereby 5.65 g of the title compound were obtained.

1. additionwere added dropwise
2. stirringthe mixture was stirred at room temperature for 13 hours
3. concentrationThe reaction mixture was then concentrated by evaporation
4. additionWater was added to the concentrate
5. extractionfollowed by extraction with ethyl acetate
6. dry with materialThe extract was dried over anhydrous sodium sulfate
7. distillationthe solvent was distilled off under reduced pressure
8. dissolutionIn 30 ml of methanol, 9.30 g of the residue were dissolved
9. additionTo the resulting solution, 30 ml of a solution of 3.51 g of potassium hydroxide in methanol were added dropwise
10. stirringby stirring at room temperature for 30 minutes
11. concentrationThe reaction mixture was concentrated by evaporation
12. extractionfollowed by extraction with ethyl acetate
13. dry with materialThe extract was dried over anhydrous sodium sulfate
14. distillationthe solvent was distilled off under reduced pressure
15. customThe residue was separated
16. custompurified by chromatography through a silica gel column (eluting solvent: n-hexane/ethyl acetate=10/1)

ORD record

ord-3e6475e429af497b9b6b41e594a0d184

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06432993B1