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

HRID 548042Notes

Reaction equation

HRID 548042 reaction equation
[Cl:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].S(Cl)(Cl)=O.Cl[CH:19](Cl)C>>[Cl:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:19])=[O:10])=[CH:12][CH:13]=1)(=[O:4])=[O:3]

Participants

4

Reactant 3

HCID 63651,1-DichloroethaneHCID 24386Thionyl ChlorideHCID 823854-(Chlorosulfonyl)benzoic acid

Product 1

HCID 4738388Methyl 4-(Chlorosulfonyl)benzoateYield 84%

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-dfd50706fe1b4b7fa381af311bd385d0
Source dataset
uspto-grants-2011_05
Patent number
US07939671B2

Reaction notes

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