Sodium Iodide → Methyl 11-iodoundecanoate

11-Bromo undecanoic acid methyl ester (20.2 g, 72.3 mmol) was dissolved in acetone (200 ml). Sodium iodide (54 g, 361 mmol) was added and reaction was refluxed under nitrogen for 16 h. After cooling to rt the salts were filtered off. The filtrate was concentrated under vacuum and water (200 ml) was added. The solution was extracted with AcOEt (2×100 ml) adding some sat. NaCl to aid phase separation. The organic extracts were pooled and washed with water (100 ml) plus a little sat. NaCl, and sat. NaCl (50 ml). Dry over MgSO4. The solution was a red-orange color. Three teaspoons of activated charcoal were added. After mixing, the solution was filtered through a bed of celite. The filtrate was concentrated under vacuum to yield a light yellow oil (20.96 g, 89%).

1. customreaction
2. temperaturewas refluxed under nitrogen for 16 h
3. filtrationwere filtered off
4. concentrationThe filtrate was concentrated under vacuum and water (200 ml)
5. additionwas added
6. extractionThe solution was extracted with AcOEt (2×100 ml)
7. additionadding some sat. NaCl
8. customphase separation
9. washwashed with water (100 ml)
10. dry with materialDry over MgSO4
11. additionThree teaspoons of activated charcoal were added
12. additionAfter mixing
13. filtrationthe solution was filtered through a bed of celite
14. concentrationThe filtrate was concentrated under vacuum

ORD record

ord-36507465f98743f99530ecba04787480

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796205B2