Acetic Acid → p-Toluenesulfonic acid

To water (288 mL), sodium hydroxide (180 g, 4.5 mol, 5.0 eq) was added. At 0° C., methanol-d3 (32.4 g, 900 mmol, 1.0 eq) was added, and the solution of tosyl chloride (206 g, 1.1 mmol, 1.2 eq) in tetrahydrofuran (288 mL) was dropwise added slowly. The mixture was warmed to room temperature and stirred overnight. The mixture was neutralized to neutral by dropwise adding acetic acid (206 g) at 25° C., filtered and partitioned. The aqueous phase was extracted with ethyl acetate (100 mL). The filter cake was dissolved in water (300 mL) and extracted with ethyl acetate (200 mL). The organic phases were combined and washed with saturated sodium carbonate (100 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate and filtered. The solvent in the filtrate was removed under reduced pressure to afford the title compound (160.5 g, purity 99%, yield 94%) as a pale yellow liquid.

1. additionAt 0° C., methanol-d3 (32.4 g, 900 mmol, 1.0 eq) was added
2. customat 25° C.
3. filtrationfiltered
4. custompartitioned
5. extractionThe aqueous phase was extracted with ethyl acetate (100 mL)
6. dissolutionThe filter cake was dissolved in water (300 mL)
7. extractionextracted with ethyl acetate (200 mL)
8. washwashed with saturated sodium carbonate (100 mL) and saturated brine (100 mL)
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationfiltered
11. customThe solvent in the filtrate was removed under reduced pressure

ORD record

ord-5ed1a2c3e032429995103dbef7ef361e

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748666B2