Dichloromethane → 1,3-Benzodioxole, 5-methyl-

Temperatur

110 °C

4-methylcatechol (15 g, 120.9 mmol) was added to a suspension of cesium carbonate (50 g, 154 mmol) in dimethylformamide (60 mL). The mixture was put under vacuum and purged with nitrogen three times. At ambient temperature, dichloromethane (15.4 g, 181.3 mmol) was added, and then the reaction mixture was heated at about 110° C. for about 2 hours. After cooling to ambient temperature, the reaction was quenched with water (500 mL) and extracted with ether-pentane (1:1 ratio, 3×500 mL). The combined organic layers were washed with water (3×1000 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford the desired product (50 g, 30%). 1H NMR (300 MHz, CDCl3) δ 6.71-6.59 (m, 3H), 5.88 (s, 2H), 2.27 (s, 3H); GC-MS: m/z=136 (MH)+.

1. custompurged with nitrogen three times
2. temperatureAfter cooling to ambient temperature
3. customthe reaction was quenched with water (500 mL)
4. extractionextracted with ether-pentane (1:1 ratio, 3×500 mL)
5. washThe combined organic layers were washed with water (3×1000 mL)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD-Eintrag

ord-ed1d0c9113a747e196f58b4e40811e98

Quelldatensatz

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07863308B2