Sodium Iodide → Methyl 11-iodoundecanoate

Temperature

22 °C

To a solution of commercially available methyl 11-bromoundecanoate (5.80 g, 20.8 mmol) dissolved in dry acetone (70 mL) was added sodium iodide (4.05 g, 27.0 mmol). The reaction mixture was stirred at room temperature (22° C.) for 19 h under an inert nitrogen atmosphere. Afterwards, the acetone was evaporated and the residue transferred into an extraction funnel with diethyl ether (100 mL) and water (40 mL). The organic phase was washed with a thiosulfate solution (5% w/v, 2×20 mL) and with water 3×40 mL. The organic phase was dried, filtered on a short column of celite and celica (1 cm/4 cm) with a mixture of hexanes:acetone as the eluent. Evaporation of the solvent gave the title compound (95%) as an oil, which was used without further purification at the next step.

1. customAfterwards, the acetone was evaporated
2. customthe residue transferred into an extraction funnel with diethyl ether (100 mL) and water (40 mL)
3. washThe organic phase was washed with a thiosulfate solution (5% w/v, 2×20 mL) and with water 3×40 mL
4. customThe organic phase was dried
5. filtrationfiltered on a short column of celite and celica (1 cm/4 cm) with a mixture of hexanes
6. customEvaporation of the solvent

ORD record

ord-4a7550b2abf14e36a9addef392993a21

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07153844B2