4-Toluenesulfonyl chloride → HCID 53643406, compound

10.0 g (58.1 mmol) of 1,4-diacetoxy-2-butene (trans/cis=85/15), 100 mL of toluene, and 50 mL of a 50% sodium hydroxide aqueous solution were added into a four-necked flask (300 mL), and thereafter, 0.936 g (2.90 mmol) of tetra-n-butylammonium bromide was added thereto as a phase-transfer catalyst. The obtained mixture was stirred at room temperature for 1 hour, and 27.7 g (145 mmol) of 4-toluenesulfonyl chloride was then added to the reaction solution. The obtained mixture was stirred at room temperature for 2.5 hours, and 100 mL of water and 50 mL of toluene were then added to the reaction solution to facilitate liquid separation. The mixture was stirred, and an organic layer was then separated. The organic layer was washed with 100 mL of water three times, and the resultant was then filtrated, while washing the residue with toluene. The obtained filtrate was concentrated at 45° C. under reduced pressure, so as to obtain 24.8 g of 1,4-di-4-toluenesulfonyloxy-2-butene in the form of a crude product of a light yellow solid (yield: 108%).

1. stirringThe obtained mixture was stirred at room temperature for 2.5 hours
2. customliquid separation
3. stirringThe mixture was stirred
4. customan organic layer was then separated
5. washThe organic layer was washed with 100 mL of water three times
6. filtrationthe resultant was then filtrated
7. washwhile washing the residue with toluene
8. concentrationThe obtained filtrate was concentrated at 45° C. under reduced pressure

ORD record

ord-3a93e9c72f654c63913d39520eb67e14

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09061991B2