반응 #2236

반응 방정식

chlorosulphonic acid

2-(methanesulphonyloxy)methoxybenzene

oxalyl chloride

toluene

Oxalyl chloride

→

title compound

3-Methanesulphonyloxy-4-methoxybenzenesulphonyl chloride

용매

dichloromethane

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   온도maintaining the temperature below 0° C
2. 2
   기타to rise to 10° C
3. 3
   기타The mixture was evaporated to dryness in vacuo
4. 4
   기타to yield an oil which
5. 5
   workup.STIRRINGwith stirring under a nitrogen atmosphere
6. 6
   workup.STIRRINGAfter stirring for 2 hours at room temperature
7. 7
   workup.STIRRINGthe reaction stirred overnight
8. 8
   기타The solvent was evaporated in vacuo
9. 9
   기타the residue was purified by column chromatography on silica
10. 10
    세척eluting with 60% ethyl acetate in hexane

실험 절차

A solution of 2-(methanesulphonyloxy)methoxybenzene (0.822 g) in dichloromethane (15 ml) was stirred and cooled to -10° C. under a nitrogen atmosphere. A solution of chlorosulphonic acid (0.27 ml) in dichloromethane (5 ml) was then added dropwise over a period of 1 hour, maintaining the temperature below 0° C. The mixture was stirred for a further 4 hours, allowing the temperature to rise to 10° C. The mixture was evaporated to dryness in vacuo to yield an oil which was suspended in toluene (20 ml) with stirring under a nitrogen atmosphere. Oxalyl chloride (0.36 ml) was added dropwise, followed by the addition of DMF (5 drops). After stirring for 2 hours at room temperature, dichloromethane (15 ml) and oxalyl chloride (0.36 ml) were added and the reaction stirred overnight. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica, eluting with 60% ethyl acetate in hexane to furnish the title compound (0.99 g) as a white crystalline solid.

출처