Methanol → HCID 123864731, compound

4-diisopropylsilanylbenzoic acid (9 g, 38 mmol)was dissolved in methanol (300 mL), and conc. H2SO4 (15 mL) was added dropwise to the solution cooled on ice. After being heated to reflux for 2 hours, the reaction solution was dissolved in chloroform (500 mL). The solution was then extracted two times with water (300 mL) and three times with 5 wt % aqueous solution (300 ml) of sodium hydrogen carbonate. An organic layer was collected and dehydrated with anhydrous sodium sulfate and filtered so that the resulting solvent was distilled out under a reduced pressure. The resulting crude product was then purified by silica gel column chromatography. After eluted with hexane having 0-5% ethyl acetate gradient, the solvent was distilled out to give a desired product (8.8 g, 93%). Its NMR data are as follows:

1. temperaturecooled on ice
2. temperatureAfter being heated
3. temperatureto reflux for 2 hours
4. extractionThe solution was then extracted two times with water (300 mL) and three times with 5 wt % aqueous solution (300 ml) of sodium hydrogen carbonate
5. customAn organic layer was collected
6. filtrationfiltered so that the resulting solvent
7. distillationwas distilled out under a reduced pressure
8. customThe resulting crude product was then purified by silica gel column chromatography
9. washAfter eluted with hexane having 0-5% ethyl acetate gradient
10. distillationthe solvent was distilled out

ORD record

ord-71220abdcba641fe924aa7700497ab26

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943758B2