Dimethyl Carbonate → 3,4-Dihydro-2-hydroxynaphthalenecarboxylic Acid, Methyl Ester

Temperature

0 °C

To a stirred solution of 2-tetralone (25.0 g, 171 mmol) in dry tetrahydrofuran (250 ml) at 0° C. under argon was added lithium diisopropylamide (111 ml, 2M solution, 222 mmol). After stirring at 0° C. for 1 h, dimethyl carbonate was added (145 ml, 1710 mmol). After stirring at 0° C. for 0.5 h, the reaction mixture was warmed to room temperature, and then heated at reflux for 16 h. The mixture was then cooled to 0° C. and quenched with hydrochloric acid (1M, 450 ml). The resulting mixture was extracted with ethyl acetate (3×1000 ml) and the combined extracts were washed with brine (1000 ml) then dried (Na2SO4) and evaporated in vacuo to afford the title compound as a dark brown oil (36.3 g, 100%).

1. stirringAfter stirring at 0° C. for 0.5 h
2. temperaturethe reaction mixture was warmed to room temperature
3. temperatureheated
4. temperatureat reflux for 16 h
5. temperatureThe mixture was then cooled to 0° C.
6. customquenched with hydrochloric acid (1M, 450 ml)
7. extractionThe resulting mixture was extracted with ethyl acetate (3×1000 ml)
8. washthe combined extracts were washed with brine (1000 ml)
9. dry with materialthen dried (Na2SO4)
10. customevaporated in vacuo

ORD record

ord-b9e614113f68465c89e5501eda65ed59

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06080752