Chloromethyl Methyl Ether → HCID 68530379, compound

Into methylene chloride (300 mL) was dissolved 3-isopropylphenol (27.24 g, 200 mmol). After cooling the solution in an ice bath, diisopropylethyl amine (69.7 mL, 400 mmol) was added in one portion, followed by the dropwise addition of chloromethyl methyl ether (18.9 mL, 236 mmol) in methylene chloride (50 mL). The reaction mixture was gradually allowed to come to room temperature. After 16 h, the reaction mixture was diluted with cold water (500 mL) and methylene chloride. The mixture was shaken in a separatory funnel and the layers were separated. The organic layer was extracted with cold water (2×500 mL), dried (MgSO4), and concentrated under vacuum. The product was dissolved in ether (200 mL) and stirred with 5 N NaOH (200 mL) at room temperature for 5 min. The ether layer was separated and extracted with cold 1N HCl (200 mL), dried (MgSO4), and concentrated under vacuum. The product was chromatographed over silica (0 to 30% EtOAc in hexane gradient), giving 20.0 g (56%) of the title compound.

1. temperatureAfter cooling the solution in an ice bath
2. customto come to room temperature
3. customthe layers were separated
4. extractionThe organic layer was extracted with cold water (2×500 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated under vacuum
7. dissolutionThe product was dissolved in ether (200 mL)
8. stirringstirred with 5 N NaOH (200 mL) at room temperature for 5 min
9. customThe ether layer was separated
10. extractionextracted with cold 1N HCl (200 mL)
11. dry with materialdried (MgSO4)
12. concentrationconcentrated under vacuum
13. customThe product was chromatographed over silica (0 to 30% EtOAc in hexane gradient)

ORD record

ord-47b76ad718ce4b32b774f444c4c5d7a8

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07511066B2