Chlorosulfonic acid → HCID 13646248, compound

HRID 1381113Notes

Reaction equation

HRID 1381113 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=1.[Cl:13][S:14](O)(=[O:16])=[O:15]>>[Cl:1][C:2]1[C:11]([S:14]([Cl:13])(=[O:16])=[O:15])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 22349978Methyl 4-Chloro-2-methylbenzoate

Product 1

HCID 13646248HCID 13646248, compoundYield 75.6%

Procedure

A mixture of 15.8 g (0.086 mol) of methyl 4-chloro-2-methylbenzoate (2) and 25.8 ml (45.2 g, 0.39 mol) of chlorosulfonic acid was heated to a gentle reflux under nitrogen. After 3 hrs., the mixture was cooled and poured slowly into an ice-water mixture. After stirring for 1 hr., the mixture was filtered and rinsed well with ice cold water. Drying in a vacuum oven (60° C.) gave 17.4 g (0.065 mol, 75% yield) of the sulfonylated acid (off-white crystals). A mixture of 14.5 g of the acid and 2 drops of dimethylformamide in 50 ml of thionyl chloride was heated to reflux under nitrogen. After 11/2 hrs., the solvent was removed under reduced pressure. Methanol (125 ml) was added to residue material and the solution was cooled to 10° C. After 5 hrs., the solid was filtered and airdried, giving 12.8 g of off-white crystals (3); m.p. 94.5° -96° C.

Workup

  1. temperaturewas heated to
  2. temperaturea gentle reflux under nitrogen
  3. temperature, the mixture was cooled
  4. filtration, the mixture was filtered
  5. washrinsed well with ice cold water
  6. customDrying in a vacuum oven (60° C.)

Sources & evidence

ORD record
ord-5fa407caf6de4ff3be4d57f2c10f3a25
Source dataset
uspto-grants-1986_04
Patent number
US04585773

Reaction notes

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