P-Toluic Acid → 3-Methanesulfonyl-4-methylbenzoic acid

HRID 1606617Notes

Reaction equation

HRID 1606617 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.Cl[S:12]([C:15]1C=C(C=CC=1C)C(O)=O)(=[O:14])=[O:13].ClC1C=C(Cl)C(S(Cl)(=O)=O)=CC=1C(O)=O>ClS(O)(=O)=O>[CH3:15][S:12]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[CH3:1])[C:6]([OH:8])=[O:7])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 7470P-Toluic AcidHCID 773362,4-Dichloro-5-(chlorosulphonyl)benzoic acidHCID 2418593-(Chlorosulfonyl)-4-methylbenzoic acid

Product 1

HCID 225978593-Methanesulfonyl-4-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 24638Chlorosulfonic acidSolvent

Procedure

4-Methylbenzoic acid (0.2 mole) is added to chlorosulfonic acid (50 ml.) and heated at reflux for about one hour, cooled and poured onto ice. The product, 3-chlorosulfonyl-4-methylbenzoic acid that separates is then employed in place of the 2,4-dichloro-5-chlorosulfonylbenzoic acid in the process described in Example 1, Step A, and then following the methods described in Steps A and B of Example 1 there is obtained 3-methylsulfonyl-4-methylbenzoic acid. This compound then is substituted for the 3-methylsulfonyl-4-chlorobenzoic acid employed in Step B of Example 55 and then by following substantially the same procedures described in Example 55, Steps B through E, there is obtained 3-furfurylamino-4-methyl-5-methylsulfonylbenzoic acid.

Workup

  1. temperatureheated
  2. temperatureat reflux for about one hour
  3. temperaturecooled
  4. additionpoured onto ice

Sources & evidence

ORD record
ord-60a8ddf997b34f408d5d1d14ad534fb7
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

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