Methanol → (3-Methoxy-2-methylpropyl)benzene

220 ml (1.9 mole) of KH (35% in oil) were placed, under a N2 -atmosphere, into a 4.5 l reactor and washed 4 times with pentane, in order to remove all traces of oil. 1.5 l of dry tetrahydrofurane were added before the dropwise addition of a solution of 259 g (1.73 mole) of 1-hydroxy-2-methyl-3-phenylpropane and 500 ml of dry tetrahydrofurane. The reaction was stirred for 15 hours at room temperature. Then 285 g (2.01 mole) of methyl iodide were added dropwise over a period of 2 hours, and stirring was continued at room temperature for another 2 hours. A possible excess of KH was hydrolyzed by adding 50 ml of methanol, then the reaction mixture was poured on ice. The product was taken up in ether, which was washed 3 times with a saturated NH4Cl solution and then with brine to neutrality. After drying over Na2SO4, the solution was filtered, concentrated and then distilled over a Vigreux-type column (boiling point: 100° C. at 5×102Pa).

1. washinto a 4.5 l reactor and washed 4 times with pentane
2. customin order to remove all traces of oil
3. stirringstirring
4. waitwas continued at room temperature for another 2 hours
5. additionthe reaction mixture was poured on ice
6. washwhich was washed 3 times with a saturated NH4Cl solution
7. dry with materialAfter drying over Na2SO4
8. filtrationthe solution was filtered
9. concentrationconcentrated
10. distillationdistilled over a Vigreux-type column (boiling point: 100° C. at 5×102Pa)

ORD record

ord-9389ecb1ff064e058e58d000cafba1be

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05939368