Iodine → 9-Dodecenoic acid

Methyl 9-dodecenoate (1273 g, 6.00 mol), water (540 mL), and isopropanol (300 mL) were added to a 5 L, 4-neck round-bottom flask at room-temperature. The flask was fitted with an over-head stirrer, condenser, a thermocouple, and an addition flask. Nitrogen was passed through the headspace for thirty-minutes while stirring. Potassium hydroxide (10 M, 660 mL, 6.60 mol) was added drop-wise over thirty-minutes. After stirring for about 45 minutes, an exotherm was observed and the mixture became homogenous. Within the next hour, stirring became impeded by formation of a gel. To re-enable stirring, an additional 300 mL of isopropanol was kneaded into the mixture with a metal spatula. The reaction was monitored by thin layer chromatography (10% EtOAc in hexanes eluent, iodine stain); reaction aliquots were quenched with aqueous hydrochloric acid, washed with water, then taken up in iPrOH. When all starting material had been consumed, the reaction was placed in an ice bath and acidified with 37% aqueous HCl (600 mL) while maintaining a temperature below 40° C. The reaction mixture was transferred into a large separatory funnel and washed with brine (3×250 mL), dried with magnesium sulfate, filtered, and dried in vacuo. The reaction was purified by vacuum distillation to give 9-dodecenoic acid (1054 g, 5.3 mol, 89% yield).

1. customThe flask was fitted with an over-head stirrer, condenser
2. waitNitrogen was passed through the headspace for thirty-minutes
3. stirringAfter stirring for about 45 minutes
4. stirringWithin the next hour, stirring
5. stirringTo re-enable stirring
6. customreaction aliquots
7. customwere quenched with aqueous hydrochloric acid
8. washwashed with water
9. customWhen all starting material had been consumed
10. customthe reaction was placed in an ice bath
11. temperaturewhile maintaining a temperature below 40° C
12. customThe reaction mixture was transferred into a large separatory funnel
13. washwashed with brine (3×250 mL)
14. dry with materialdried with magnesium sulfate
15. filtrationfiltered
16. customdried in vacuo
17. distillationThe reaction was purified by vacuum distillation

ORD record

ord-6af3438928254790948890b6c2fc949a

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045447B2