Hydrochloric Acid → Methyl 2-(4-(2-hydroxyethyl)phenyl)-2-methylpropanoate

In a reaction vessel, 4-bromo phenethyl alcohol (5.0 g), hexamethyldisilizane (HMDS; 3.0 g), acetonitrile (25 mL) and ammoniumchloride (0.01 g) were introduced, and the mixture was stirred at room temperature for 1 hours or more. The mixture was condensed under reduced pressure, and dichloromethane (30 mL) and distilled water (20 mL) were added to separate layers. The separated organic layer was dehydrated with Na2SO4, and then, condensed by filtration. And then, Pd(dba)2 (0.29 g), t-Bu3P (0.20 g), ZnF2 (1.28 g), methyltrimethylsilyl dimethylketene acetal (2.2 g) and DMF (50 mL) were added thereto, and the mixture was reacted at 80° C. for 18 hours. Distilled water (75 mL), ethylacetate (75 mL) and 1N hydrochloric acid (9 mL) were added thereto, and the mixture was stirred to separate layers. The separated organic layer was dehydrated with Na2SO4, and then condensed by filtration, and purified to obtain 2-[4-(2-hydroxy-ethyl)-phenyl]-2-methyl-propionic acid methylester (5.2 g, yield 88%).

1. distillationdistilled water (20 mL)
2. additionwere added
3. customto separate layers
4. customcondensed
5. filtrationby filtration
6. additionAnd then, Pd(dba)2 (0.29 g), t-Bu3P (0.20 g), ZnF2 (1.28 g), methyltrimethylsilyl dimethylketene acetal (2.2 g) and DMF (50 mL) were added
7. customthe mixture was reacted at 80° C. for 18 hours
8. stirringthe mixture was stirred
9. customto separate layers
10. customcondensed
11. filtrationby filtration
12. custompurified

ORD record

ord-164744fff9884534b9a5ab8d67f68168

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367704B2