1,1-Dichloroethane → Methyl 4-(Chlorosulfonyl)benzoate

Temperature

0 °C

4-Chlorosulfonyl benzoic acid (5 g, 23 mmol) and thionyl chloride (20 mL) in dichloroethane (10 mL) was heated to 80° C. for 2 hr. The reaction mixture was concentrated via rotary evaporation to give a brownish solid. The solid was chilled on ice for 5 minutes and ice-cold methanol (40 mL) was added with stirring at 0° C. for 5 minutes. The reaction mixture was allowed to warm to ambient temperature and stirred an additional 10 min. The addition of ice-cold water (40 mL), produced a white solid that was collected by filtration and dried under vacuum to afford pure methyl 4-(chlorosulfonyl)benzoate (4.5 g, 84%). 1H NMR (400 MHz, DMSO-d6): δ, ppm: 3.84 (s, 3H), 7.70 (d, 2H, J=8.4 Hz), 7.93 (d, 2H, J=8.4 Hz).

1. concentrationThe reaction mixture was concentrated via rotary evaporation
2. customto give a brownish solid
3. temperatureThe solid was chilled on ice for 5 minutes
4. temperatureto warm to ambient temperature
5. stirringstirred an additional 10 min
6. customproduced a white solid
7. filtrationthat was collected by filtration
8. customdried under vacuum

ORD record

ord-5083706653c14298bb2cf0665cb3da7d

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445692B2